Wondering what to pack for Chicago? You’ll obviously want to consider the season’s weather and the activities on your itinerary. And then there are those essential items that will make your trip easier and more comfortable.
What to Pack for Chicago
Follow the Chicago packing list below to make sure you have everything you need for your Windy City getaway.
Tote-Backpack Combo Bag
Many famous writers have Chicago connections—like Gwendolyn Brooks, Studs Terkel, Carl Sandburg, Theodore Dreiser, David Mamet, Nelson Algren, Scott Turow, Sandra Cisneros, Shel Silverstein, and Harriet Monroe, to name a few. So an anthology of work by some of the city’s storied writers and new voices should top your list of what to pack for Chicago.
The thrice-raised crusts on the deep-dish pizzas at My Pi are airy inside and crispy outside, while the four-cheese filling blends locally made mozzarella and artisanal cheeses from Wisconsin dairies. As well as multiple traditional toppings, Mi Pi features a Hawaiian pineapple-smoked ham pizza. Locals also love the white pizza topped with a basil-pesto sauce. The Bucktown location is a no-frills storefront that’s primarily for pick-up and delivery. For a sit-down meal, head to the suburban Northbrook location.
The Hotel Lincoln is known for its friendly Midwestern hospitality, with 185 guest rooms featuring comfortable heartland style and works by local artists. The Kennison restaurant serves contemporary American cuisine, and J. Parker Rooftop Bar overlooks leafy Lincoln Park. It’s an easy stroll to restaurants, music venues, comedy clubs, Lincoln Park Zoo, DePaul University, and the historic Old Town neighborhood. A 10-minute bus or bike ride gets you to Lake Michigan beaches and bustling North Michigan Avenue shopping.
Amenities: Jonathan Adler bath products, 24-hour fitness center, coffee bar grab-and-go snacks, flat-screen HD TVs, iHome docking stations, and complimentary bikes.
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Lincoln Park Zoo
As one of the world’s largest science museums, the Museum of Science & Industry in Hyde Park is one of the most popular places to visit in Chicago—especially for families. Headliner exhibits include the only German World War II U-505 submarine ever captured and the “Science of Storms” simulation of tsunamis, tornadoes, and avalanches. Kids love the underground coal mine and “The Great Train Story,” an exhibit of 20 model trains traveling through miniature U.S. landscapes between Seattle and Chicago.
Nancy and Rocco Palese’s claim to Chicago deep-dish pizza fame is creating the “stuffed pizza,” modeled after their Italian family’s Easter cake recipe. Like a pie, the pizza has two layers of dough sandwiching melted mozzarella and layered fillings. Then tomato sauce is slathered on the top crust. The roasted garlic, sauteed onion, and seasoned baby spinach filling are garden fresh. Carnivores love the Italian sausage, Canadian bacon, and pepperoni fillings. Nancy’s Pizza has numerous takeout and delivery locations around Chicagoland.
Despite the Windy City’s rep for bad weather, the sun actually shines here quite often—so your coolest pair of polarized shades belongs at the top of your list of what to pack for Chicago. We like classic styles for sashaying down tony Michigan Avenue, reflecting glare from mounds of snow in Chicago’s parks, sipping cocktails at sunset at a rooftop lounge, or sunbathing at one of the lakefront beaches.
Even before the Cubs became the 2016 World Series champions, their home field ranked as a top Chicago attraction. Built in 1914, the nation’s second-oldest baseball park sports a classic grass field, hand-turned scoreboard, old-school bleacher seats, and ivy-strewn walls. Behind-the-scenes ballpark tours are offered seasonally, and concerts held in this historic sports venue knock it out of the park.
A crushable, reusable water bottle should be on your Chicago packing list to keep you hydrated on the go.
Chicago is a kid’s kind of town. Families find plenty of things for kids to do in Chicago year-round including interactive museums, kid-friendly educational tours, lively historical sites, and fun outdoor activities. Best of all, lots of these experiences are free.
What to Do in Chicago with Kids
Family fun in Chicago is nonstop—just like your children! Discover nine exciting activities to do in Chicago with kids.
As if a 200-foot Ferris wheel, an IMAX theater, live music, boat rides, and an indoor garden of leaping fountains weren’t enough for families to enjoy on Navy Pier, there’s the Chicago Children’s Museum, too. Daily arts programming and more than a dozen exhibits about nature, sports, safety, science, art, and architecture are geared for kids up to 10 years old. At Navy Pier’s internationally acclaimed Chicago Shakespeare Theater and its new 850-seat venue called The Yard, families experience the Bard’s works and other visiting international performances. One of the most fun things to do in Chicago with kids is a Lake Michigan boat ride. Families love the thrilling speedboat Sea Dog and the pirate-themed sails aboard schooner Tall Ship Windy. Spectacular, free fireworks shows at Navy Pier light up the summer skies on Wednesday and Saturday nights.
Lincoln Park Zoo
Just 15 minutes from the Loop, 1,208-acre Lincoln Park is one of the most fun places for kids in Chicago. The lakefront park has a huge sandy beach, baseball diamonds, bike paths, a public golf course, a free zoo and two family-friendly museums. The Chicago History Museum introduces visitors to the city’s rich cultural, industrial, political, and sports history. The hands-on “Sensing Chicago” exhibit engages little ones. Daily baby butterfly releases at the butterfly haven in the Peggy Notebaert Nature Museum delight kids, as do the interactive exhibits about Illinois’ natural environment. Recently restored and expanded Theater on the Lake stages summer performances while the prairie-style theater building’s restaurant serves upscale Midwest fare year-round.
More than 1,200 animals live at this 49-acre, free neighborhood zoo opened in 1868. An African penguin colony waddles around the Robert and Mayari Pritzker Penguin Cove. Polar bears swim and lumber about the Walter Family Arctic Tundra. Japanese snow monkeys soak in pools at the Regenstein Macaque Forest. Daily educational programs and special seasonal events, such as ZooLights over the holidays, attract both local and visiting families.
Biking & Segway Tours
You can cover a lot of ground wheeling around Chicago. Here are two of our favorite rolling tour operators to help you experience Chicago with kids. The two-hour, 4.5-mile Tike Hike from Bobby’s Bike Hike is a bike tour for families with kids age 10 and under. For teens, try the Electric Bikes @ Night Tour or the Southside Old Chicago Gangster Tour, which includes sampling Chicago’s famous Italian beef sandwiches. Absolutely Chicago Segway Tours offers 10 themed itineraries along the lakefront, Michigan Avenue, and Chicago River. Safety-conscious guides instruct riders on how to operate the easy-to-maneuver Segways before leading guests on two-hour tours covering city history, architecture, and culture. Children must be at least 12 years old to ride.
Chicago Cultural Center
Visitors stand in a kaleidoscope of pastel-colored light beneath the world’s largest Tiffany stained-glass dome at the free Chicago Cultural Center, constructed in 1897 as the city’s first public library. Now it hosts free concerts, lectures, family-friendly films, art exhibits, and theater performances. Take a free guided tour highlighting the landmark’s history, beautiful marble and mosaic interior, Tiffany dome, and ornate Grand Army of the Republic Hall.
Maggie Daley Park
One of the most fun places for kids in Chicago is Maggie Daley Park in the northeast corner of Grant Park. Open year-round, the park offers 20 acres of trees, gardens, and elevated, landscaped vantage points for stunning views of Lake Michigan and Chicago’s iconic skyscrapers. Kids clamber across massive suspension bridges, climb ropes, and glide down twisting slides. Fees are charged for the 40-foot climbing wall and miniature golf, both open spring through fall. The winter ice skating ribbon is free with skate rentals available.
Garfield Park Conservatory
Designed by landscape architect Jens Jensen and built in 1908, this 2.8-acre, crystal-roofed greenhouse ranks as one of the world’s largest conservatories. Admission is free for visitors to wander serpentine paths through nearly 10,000 plant varieties. Families dig the Children’s Garden, a greenhouse blooming with child-friendly vegetation and giant sculptural displays showing a plant’s life cycle. Free weekly drop-in programs include mini greenhouse tours, seed planting workshops, storytelling, and concerts. Kids make mud pies and scramble around a tree trunks obstacle course in the Play & Grow Garden, while the Sensory Garden features seasonal beekeeping demonstrations.
Chicago Lakefront Beaches
A day at the beach is one of the most popular summer activities in Chicago with kids. You can swim, paddle, walk, bike, sail, play volleyball, and build sandcastles at Chicago’s Lake Michigan beaches. Many beaches have lifeguards on duty; more than half are handicap-faccessible; and all are free and open year-round. The best two beaches for families are both within 15 minutes of the Loop. Chill for a day on the sprawling sands of lifeguard-monitored North Avenue Beach, where an open-air sports facility offers roller hockey, dodge ball, and fitness classes. Rent kayaks, paddleboards, wakeboards, Jet-Skis, and lounge chairs at the vintage ocean liner-shaped bathhouse-concessions building. Close to Navy Pier on a protected inlet, quiet Ohio Street Beach is perfect for novice swimmers and sand-digging toddlers.
Just 30 minutes west of the city, Brookfield Zoo is a fun place to go in Chicago with kids. You’ll undoubtedly find your favorite animal among the more than 2,000 creatures living on the zoo’s 216 acres—including polar bears, grizzlies, bald eagles, and 2,000-pound bison. Kids can talk with animal trainers, help feed some critters, and check out hands-on exhibits and arts programs. You can also take a quiet, quarter-mile stroll around the lake in the Salt Creek Wilderness area, a perfect place to picnic.
Bartoli’s Pizzeria’s connections to Chicago-style pizza run deep. Owner Brian Tondryk’s grandfather is Fred Bartoli, one of the founders of the Gino’s East empire. Bartoli’s Pizzeria takes a twist on proven family recipes, lacing its cracker-crunch crust with parmesan cheese. Cheddar, provolone, and salty gorgonzola add flavor layers to the mozzarella base. Regulars rave about the house-made Italian sausage and fresh veggies.
My Pi Pizza
If “more” is your motto, Giordano’s is your Chicago-style pizza. The pies are super dense and the toppings many. Plus, you’re never far from a Giordano’s. The chain has numerous restaurants throughout Chicagoland, each reflecting the neighborhood’s vibe. Giordano’s “stuffed pizzas” come chock-full of gloppy mozzarella and mounds of fresh ingredients, with a minimum of five fillings. There’s a cheese-only option as well as some adventurous versions such as one with bacon and barbecue chicken. You can also order a “Make Your Own Deep-Dish” customizable pie.
Chicago’s claim to pizza world fame is the creation of deep-dish pizza. The answers to who invented it and where to find the best Chicago-style pizza depend entirely upon who you ask. But there is one thing Chicagoans can agree on: It’s all about the crust. Chicago deep-dish pizza is always a delicious, gloppy, gut-bustin’ meal requiring a fork and knife to eat. The average bake time for a large custom-built pie is 30 minutes, so don’t go to the restaurant hangry.
Where to Find Chicago Deep-Dish Pizza
To sink your teeth into a delicious local tradition, try one of these restaurants dishing up the best Chicago deep-dish pizza.
Want a little bling during your Chicago getaway? Keep things simple with a pair of classic earrings. Choose smooth surfaced studs or hoops with secure back-of-the-ear closures because it’s easy to catch more intricate earrings when removing a scarf or hat. Always pack extra earring backs.
Although bigger than most boutique hotels in Chicago, this 452-room property still offers plenty of personal touches. LH Rooftop, a seasonal terrace bar and restaurant serving craft cocktails and small plates, is the place to be in Chicago on summer evenings, especially at sunset. Views also impress from LH on 21, a year-round bar and restaurant serving American fare. Spacious guest rooms and suites feature sleek woods, crisp white linens, and minimalist but comfortable furnishings. Enjoy a contemporary take on afternoon tea at Bridges Lounge.
Amenities: 55-inch HDTVs, Chromecast entertainment streaming, 24-hour fitness center, room service, and full-service spa.
The Alise Chicago
A contender for the title “deep-dish pizza don” is Lou Malnati, founder of the Lou Malnati’s Pizzeria chain. After working as a pro pizzaiolo in local pizzerias (including Uno), Lou opened his own place in 1971. Today, his sons run the deep-dish dynasty with restaurants throughout the city and suburbs. The signature “Lou” pie is composed of a crisp, Italian breadstick-like crust layered with a mozzarella-cheddar-Romano cheese blend, spinach-mushroom mix, Italian sausage, and sliced Roma tomatoes.
Chicago Pizza and Oven Grinder Co.
Layers of expressive graffiti scrawled on every surface in the original Gino’s East restaurant downtown attest to its popularity since opening in 1966. Gino’s creative decor and signature cornmeal crust make it a top choice for Chicago deep-dish pizza. Crunchy-edged dough encircles a cheesy center melding toppings together. The spinach-tomato pizza margherita always satisfies, while the Chi-talian Stallion pizza sports spiced roast beef, giardiniera (an Italian relish), and roasted sweet peppers, all borrowed ingredients from the classic Chicago Italian beef sandwich. Pair your pizza with one of the craft beers brewed on site at Gino’s River North pizzeria/pub and comedy club.
Located in Chicago’s historic Gold Coast neighborhood, the Talbott Hotel was a stately 1920s apartment building before becoming one of the best boutique hotels in Chicago. The 178 guest rooms and suites are decorated in calming neutrals with splashes of vibrant color. Plush fabrics, luxury linens, textured wall coverings, and carved woodwork surround pampered guests. The 20 East restaurant serves modern American fare all day, as well as craft beers, wines, and cocktails.
Amenities: Marble-accented bathrooms, waterfall showers, Jonathan Adler amenities, La Bottega bathrobes, LG Smart TVs, 24-hour room service, and 24-hour fitness center.
Kimpton Gray Hotel
Chicago inspires creativity in everyone. While digital photographs capture the scene in a second for social sharing, old-school written documentation can be just as meaningful. Record your own descriptions and sketches in this unlined journal.
Rain happens, so be ready to fend off the drops with a compact, sturdy umbrella. Bring a gallon-sized, plastic zip-lock bag for dry storage in your bag when the sun shines again. The Repel Windproof Travel Umbrella claims to be wind-proof.
Thompson Chicago, located in the tony Gold Coast neighborhood, is steps from Lake Michigan’s Oak Street Beach and the shops of the Magnificent Mile, making it one of the most popular boutique hotels in Chicago. A massive stone fireplace blazes in the prairie-style lobby, and the 248 guest rooms and suites exude a calm-cool vibe through minimalist furnishings and an earth-toned color palette. Floor-to-ceiling windows frame glittering city and Lake Michigan views. On-site restaurant Nico Osteria features seafood-focused Italian cuisine.
Amenities: Spacious bathrooms, rain showers, Frette terrycloth robes, IPTV, SFERRA linens, 24-hour room service, 24-hour fitness center, and complimentary luxury car transport to nearby locations.
Virgin Hotels Chicago
Chicagoans call 319-acre Grant Park their “front yard” because it’s their favorite place to promenade, picnic, party, and play. Grant Park encompasses several smaller green spaces, including Millennium Park, where must-see Chicago attractions include the giant bean-shaped “Cloud Gate” sculpture, the digitally animated Crown Fountain, the Art Institute of Chicago, and the Harris Theater for Music and Dance. At Maggie Daley Park, families clamber up a climbing wall and, in winter, skate the ice ribbon. On Grant Park’s south end are historic Buckingham Fountain and the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium. Sprawling green lawns along the lakefront stage Chicago’s blockbuster festivals including Taste of Chicago, Lollapalooza, and Chicago Blues Festival.
Art Institute of Chicago
Pizzeria Uno claims to have invented Chicago deep-dish pizza in 1943. The iconic River North restaurant is in a converted brick townhouse. “Dense” describes both Uno’s dining room at prime eating hours and the pie’s thick, gooey goodness. Doughy, golden-brown crust encircles slabs of melted mozzarella cheese layered with flavor-packed crushed tomatoes. Toppings include sausage, pepperoni, meatballs, and veggies. Can’t wait? Opt for a to-go single slice, a popular lunch choice among area office workers.
Lou Malnati’s Pizzeria
Rudy Malnati, Jr.—part of the second generation of the Lou Malnanati deep-dish pizza family—opened Pizano’s Pizza & Pasta in 1991. Chicago sports pennants and player photos hang on the paneled walls of the Loop location, a big lunch spot and after-work hangout. Pizano’s stellar rep rests on its crumbly buttery crust, a secret family recipe. The signature pie is the sausage-mushroom combo “Hey Hey” Jack Brickhouse Special. Thick, tangy crushed tomatoes and savory combos of meats and vegetables top these deep-dish pizzas. However, Pizano’s parts ways from Chicago-style pizza tradition by also offering a carb-free sausage crust.
When trolling for the best pizza in Chicago, Pequod’s deep-dish is a real catch. The Lincoln Park restaurant is named after the whaling ship chasing Moby-Dick in Melville’s classic novel—hence the funky, graffiti-style artwork of a badass albino whale. Baked in a blackened cast-iron pan, Pequod’s focaccia-style crust harbors a thick cheese layer. It oozes to the pan’s edges and darkens while cooking into a crispy caramelized ring rimming the pizza’s outer edge. Fresh topping choices abound like fish in the sea, but the Italian sausage or meatballs with sauteed onions and anchovies really float my boat.
Pizano’s Pizza & Pasta
It’s easy to spend a day or two in these three top-notch museums on the lakefront Museum Campus, one of the most popular places to visit in Chicago. Dolphins, beluga whales, penguins, and an 80-year old lungfish are just a few of the 32,000 animals living at Shedd Aquarium. Don’t miss the Caribbean Reef exhibit, where divers hand-feed sharks and exotic fish. Adler Planetariumwows visitors with ever-changing, high-tech celestial sky shows and space exploration exhibits, including the Gemini 12 spacecraft. The Field Museum of Natural History ranks high on visitors’ Chicago sightseeing lists to meet Sue, the largest complete Tyrannosaurus rex ever unearthed. Another crowd pleaser is the “Inside Egypt” exhibit, displaying real mummies.
The venerable Art Institute of Chicago showcases one of the world’s largest permanent collections of Impressionist paintings in addition an extensive assortment of Chinese bronzes, medieval arms, American art, and contemporary masterpieces. Take in vibrant Marc Chagall’s vibrant stained-glass “American Windows” installation, or wander through the charming Thorne Miniature Rooms displaying dollhouse-sized rooms decorated in every historical interior design style. Short on timme? Select one or more of the free themed mini-tours.
British entrepreneur Richard Branson fancied Chicago for his first Virgin Hotels property in the United States, and the result was this art deco-style property in the Loop near the theater district. Called “chambers,” 250 guest rooms and suites feel like modern apartments. Sliding doors separate the bathroom and dressing area from the “Sleeping Lounge.” Lipstick-red accents include a Smeg fridge and London Underground-themed rug. The playful in-room amenities, whimsical decor, edgy on-site entertainment, and cleverly designed spaces make Virgin Hotels Chicago one of the most distinctive Chicago boutique hotels. Meet friends and make new ones at the Commons Club’s nightly hosted social hour. Seasonal rooftop bar Cerise is a local hot spot known for cozy-up couches, vibrating DJ parties, and skyscraper-studded views.
Amenities: Rain showers, makeup vanities, Red Flower Palo Santo bath products, fitness center, coffee/wine bar, 24-hour room service, and “Lucy” free mobile app to customize your experience.
Each of the many boutique hotels in Chicago has a personality all its own. Whichever one you choose, you can count on attentive service, luxurious amenities, and extra conveniences in a distinctive setting reflective of the Windy City.
Chicago Athletic Association Hotel
Plenty of people head straight for shopping trip down the Magnificent Mile or to one of its many high-end restaurants when they visit Chicago, but the world-class city is just as accessible to those on a budget, too. Here, a round-up of our favorite free activities in the Windy City that prove its many attractions are availble to everyone.
1) Get up close and personal with the new Mangalitsa piglets at the Lincoln Park Zoo’s “Farm-in-the-Zoo.” While you’re there, why not wander over to see the red pandas, too?
2) Experience the sounds of the Chicago Jazz Festival in Millennium Park. This year there’s a special tribute to the music of Billy Strayhorn and a special appearance by celebrated chanteuse Dee Dee Bridgewater.
3) Squeeze in a workout in the sun on Saturday mornings, with free yoga, tai chi, and pilates classes on the Great Lawn in Millennium Park.
4) Check out one of more than 200 free concerts that the Chicago Cultural Center hosts every year. A bonus if it takes place in the Preston Bradley Hall, which has the world’s largest Tiffany dome.
5) Interested in exploring a new neighborhood? Make an appointment with a Chicago Greeter, and you can get one of three dozen insider tours throughout the city.
6) Look over the three millennia of Middle Eastern treasures at the Oriental Institute, part of the University of Chicago in Hyde Park. The human-headed winged bull, a 16-foot-tall, 40-ton relief, dominates the Mesopotamian Collection in the Khorsabad Court.
7) Learn about social reformer Jane Addams at the Hull-House Museum on the University of Illinois at Chicago campus. You’ll find a mix of exhibits on her efforts to improve the lives of the poor, which includes one focused on the importance of play.
8) There’s flora for everyone at the Garfield Park Conservatory, which contains spectacular aroids, a lush fern room, and a fine children’s garden, complete with play area. Don’t miss the “Persian Pool” and its collection of site-specific glass pieces by Dale Chihuly.
9) Experience a sunset along The 606 with a walk, stroll, or run. Chicago’s elevated park has excellent views of the skyline, and along the way you’ll see great murals and an outdoor observatory.
10) From ancient Chinese pottery to Picasso, the Smart Museum at the University of Chicago is a great place to spend an afternoon. The outdoor sculpture garden features works by Richard Hunt and Louise Nevelson.
11) Located just north of the Lincoln Park Zoo, the Alfred Caldwell Lilly Poolis a perfect respite from the surrounding bustle in any season. The treasures here include a council ring, an expansive range of well-tended Midwestern plant life, and a prairie-style pavilion.
12) With galleries profiling everything from North Korean society to monumental architecture from around the world, the Museum of Contemporary Photography at Columbia College is a gem. If you’re lucky, you might be in town for one of their exhibition openings or engaging talks.
13) To explore the National Museum of Mexican Art is to know the breadth of the Latino experience, in Chicago and beyond. On any given visit, you might see an exhibit on immigration narratives or another on Mexican psychedelia.
14) A walk around the Crystal Gardens on Navy Pier is the perfect activity on one of those predictably freezing Chicago winter days—or any other time of year. Look up and view 80-plus palm trees, “leapfrog” fountains, and a range of distinctly non-native foliage.
15) Millions enter the Water Tower Place Mall ever year for intense shopping, but how many walk across the street to the original Water Tower’s City Gallery? It’s a tiny marvel on Michigan Avenue, and you might find a photographic tribute to Charlie Trotter or an exploration of Chicago’s printmaking traditions within.
16) Inside the Harold Washington Library Center, visitors can make their way through more than 50 pieces of public art. Jacob Lawrence’s bright and exuberant celebration of the late Harold Washington, an inveterate reader and the first African American mayor of Chicago, is centrally located inside the main lobby.
17) Ever wanted to hear John C. Reilly as Abraham Lincoln? David Schwimmer as the Bean (a.k.a. Cloud Gate)? It’s all possible via the Statue Stories Chicago program. Just swipe your phone on the statue’s tag to hear more than two dozen sculptures come to life as you visit them all around the city.
It’s easy to burn through your cell phone juice snapping pictures around the city and posting them on Instagram. Maintain 100 percent power with a small but mighty high-speed charger.
Overnighting in this National Historic Landmark is anything but staid. It’s an adventurous, laid-back Chicago boutique hotel stay. The Reliance Building, now The Alise Chicago, was one of the world’s first skyscrapers, built in 1895. The Loop hotel’s public spaces and 122 guest rooms and suites are decorated with original architectural details including mahogany woodwork, wrought iron ornamentation, coffered ceilings, and marble floors. Standard guest rooms can feel a bit tight, but the bay windows flood them with natural light and expansive State Street views. The popular Atwood restaurant serves modern American meals all day. Each afternoon guests snack on free, mini-pineapple cupcakes in the comfortable lobby.
Amenities: Nightly complimentary wine receptions, 24-hour fitness center, flat-screen TVs, room service, robes, slippers, and free bikes.
Fortunately for visitors, many of the most popular Chicago attractions are concentrated downtown and within a scenic walk from one another. That means it’s easy to put together a Chicago sightseeing itinerary that will keep you entertained without wearing you out.
Must-See Chicago Attractions
Ask a Chicagoan what it’s like to live here and love it, and he or she will probably point you to the following unforgettable Chicago attractions.
Chicago Architectural River Cruise Tour
The Oriental Institute
Chicago’s prime beach season runs from Memorial Day weekend through Labor Day, but many hotels have beautiful indoor pools with stunning city views, open year-round. Whenever you visit, you’ll want to pack your swimsuit.
Windy City weather can be just that. Whether you’re sporting a ponytail, waterfall braid, or man bun, hair ties will come in handy to keep tendrils from blowing into your camera lens.
There’s no better way to experience the city’s architecture, dining, and nightlife than strolling the Chicago Riverwalk stretching from Lake Michigan west to Franklin Street. The continuous waterfront walkway passes iconic skyscrapers, tiered gardens, public art, and spouting fountains. Chicago Riverwalk activities include boat cruises, kayak rentals and tours, pier fishing, and Audubon-guided bird walks. Learn about the waterway’s history and its moving bridges at the McCormick Bridgehouse & Chicago River Museum.
The Ledge at Willis Tower
A stroll down Michigan Avenue is simply required of all Chicago visitors. (A romantic horse-drawn carriage ride counts, too!) The famous boulevard known for its luxury hotels, historic landmarks, and entertainment venues traces the original shoreline of Lake Michigan. The blocks from Oak Street south to the Chicago River are called the “Magnificent Mile,” a swank shopping and dining district. Hidden gem Chicago attractions tucked into Michigan Avenue skyscrapers include the American Writers Museum, Chicago Sports Museum, Spertus Institute of Jewish Learning and Leadership, and Pritzker Military Museum and Library. Duck into the Chicago Cultural Center to see the world’s largest Louis Comfort Tiffany glass dome.
With debut restaurants from young-gun chefs and new projects from Chicago legends, this great dining city stays on its toes.
This Gold Coast newcomer, opened in the Ambassador Chicago in late 2017, began its life over 80 years ago as the iconic and oh-so-exclusive Pump Room — a favorite of visiting stars from Josephine Baker to Mick Jagger. It’s been revived in style following a rebrand of the hotel, with chef Doug Psaltis turning out refined dishes that hearken back to the original restaurant’s heyday: lobster Louie, Dover sole, and even an original 1954 cheesecake recipe. Entrées $19-$49.
Pacific Standard Time
Chef Erling Wu-Bower cut his teeth under the legendary Paul Kahan at beloved Chicago talent incubators the Publican and Nico Osteria. Now, after much anticipation, he’s struck out on his own as head chef and co-owner of a restaurant with partner Joshua Tilden. PST’s West Coast-inspired menu skips the clichés of California cuisine — no artfully arranged figs and goat cheese here — in favor of hearth-fired flatbreads, bright vegetables, and plenty of seafood. Entrées $15-$35.
After closing the dearly-departed Snaggletooth last summer, Chef Jennifer Kim heads to Andersonville and comes back in full force with this self-described purveyor of “fun Korean fare.” Drawing on family recipes and a healthy dose of Italian technique, her menu mixes the traditional (kalbi, seasonal banchan) with experiments in texture and flavor, like Calabrian chili-crusted Korean fried chicken and ddukbokki stewed in a lamb’s neck ragu. Entrées $12-$19.
Mi Tocaya Antojería
Chicago native Diana Dávila earned her culinary chops both in the kitchen and in the field: she grew up helping at her family’s tacqueria and spent her summers in Mexico, ultimately studying at Susana Trilling’s famed Oaxacacooking academy. The menu at her colorful Logan Square hangout — which earned her a Best New Chef nod from Food & Wine this year — turns a fresh eye to the many iterations of Mexican cuisine, with dishes like mole amarillo topped with bright fiddlehead ferns and the Sunday dinner special of fried chicken and churros. mitocaya.com; entrées $10-$26.
The team behind Sepia — one of the city’s many Michelin-starred New American institutions — decided to loosen up some buttons with their new restaurant next door. Sepia’s Andrew Zimmerman does double duty as Proxi’s executive chef, curating a livelier, more mix-and-matchable menu of small plates. Fire is the uniting force, smoking pumpkin for a savory paratha and coal-roasting mussels to be drowned in njuda butter. proxichicago.com; entrées $12-$30.
This stylish Loop hotel in a converted office building features 291 soothing guest rooms and suites decorated in muted gray, cream, and light blue. The Steadfast restaurant serves contemporary American cuisine with global nuances. Lots of deals have been brokered over cocktails at clubby, library-themed Vol. 39’s intimate bar. Boleo, a rooftop restaurant and lounge on the 15th floor, dishes up small plates inspired by Peruvian and Argentinian street food and hosts late-night DJ dance parties.
Amenities: Complimentary nightly guest social hours, in-room yoga mats, 24-hour fitness center, room service, free bikes, hair salon, children’s books checkout, complimentary morning coffee/tea, and “Forgot It? We Got It!” travel essentials program.
A Chicago sightseeing experience wouldn’t be complete without immersing yourself in the city’s architectural history aboard a Chicago River cruise. The 90-minute Chicago’s First Lady cruises, run by the Chicago Architecture Foundation, incorporate city history into tours focused on explaining architectural styles represented by more than 50 buildings flanking the Chicago River. Chicago Line Cruises‘ 90-minute tours, associated with the Chicago History Museum, discuss architecture in historical context, including the Great Chicago Fire of 1871 that gave rise to the legendary skyscrapers and soaring glass towers visitors marvel at today.
Boston: Drinking & Nightlife
Backpacks are perfect for trouncing around town with all your stuff, but you don’t have to sacrifice style for a roomy, easy-to-carry bag. This backpack-tote combo made of water-resistant fabric delivers ample interior space, multiple compartments, and secure zipper enclosures, plus both a sturdy top handle and a long, crossbody shoulder strap. For a more unisex option, this bagconverts from a messenger bag, to a backpack, and into a briefcase.
The Blackstone is a historic, grand dame hotel built in 1910, and one of the most popular boutique hotels in Chicago. Facing Grant Park, the 331-room South Loop property offers travelers modern comforts amidst luxurious Old World grandeur. Guests can walk to Lake Michigan, the Art Institute of Chicago, the Museum Campus, and State Street shopping. Well-appointed guest rooms and suites are decorated in rich shades of brown, pewter, copper, and robin’s egg blue, contrasting with tailored white bed linens and shiny brass accents. Restaurant Mercat a la Planxa serves tapas and craft cocktails inspired by Catalan cuisine. Free in-room Wi-Fi is available for Marriott Rewards members.
Amenities: Spacious marble bathrooms, La Bottega amenities, luxury bedding, 24-hour fitness center, and evening-only room service.
Chicago is just as beautiful in winter as it is in warmer seasons. You can keep your hands warm without sacrificing photo opportunities with these fingerless gloves.
While phone cameras take great photos, SLR digital cameras take even higher-quality images and offer greater creative control for serious shutterbugs. Here’s a Chicago photo tip: Capture a panoramic shot of the iconic skyline rising from the lake or silhouetted against a golden sunset from the Adler Planetarium on the Museum Campus peninsula.
Portable Cell Phone Battery Charger
This 1893 landmark building recently was converted into one of the best boutique hotels in Chicago. The 240-room hotel blends Old World elegance, modern amenities, and clubby flair. Six dining establishments range from Shake Shack to farm-to-table fare in the swanky Cherry Circle Room. The Game Room sports the athletic club’s original indoor bocce court plus billiards, shuffleboard, and chess/checkers tables. Check stunning views of Lake Michigan and Millennium Park from Cindy’s, the hotel’s rooftop restaurant.
Amenities: Carrara marble bathrooms, rain showers, C.O. Bigelow bath products, 42-inch flat-screen TVs, SFERRA bed linens, 24-hour fitness center, 24-hour room service, and free bicycles.
Because sometimes you really need silence.
Chicago Pizza and Oven Grinder Co.’s ingenious take on deep-dish—a single-serving pizza pot pie—makes it a contender for the best pizza in Chicago. The golden disk of thrice-raised, fluffy Sicilian-style bread crust encases a savory center of melted cheeses, butt pork sausage, and button mushrooms swirling in a garlic/onion/pepper/plum tomato sauce. A veggie-only version is available too. These pot-pie pizzas come in half- or one-pound sizes. During standard dining hours expect a long wait to be seated.
Chicago sightseeing reaches new heights at the Willis Tower’s Skydeck on the 103rd floor. Visitors can survey city and lake views as far as the eye can see—and that’s into three neighboring states on a clear day. For an extra adrenaline rush, step onto The Ledge to gaze down from one of four cantilevered glass boxes suspended 1,353 feet above the busy Loop streets.
Museum of Science & Industry