Top Things to Do in Chicago | Midwest Living

Top Things to Do in Chicago

Museums, shopping, a free zoo, an off-the-beaten-path Mexican restaurant, a hotel for social travelers—here's our guide of what to do, where to eat and where to stay in Chicago.

On the western shore of Lake Michigan, the Midwest’s biggest city blends outdoor recreation and cosmopolitan luxuries. Millions visit each year to shop the Magnificent Mile, explore Millennium Park and cheer on one of the seven pro sports home teams. Jazz clubs and theaters keep the party going into the night. 

What to do

Adler Planetarium The exhibits get a little technical for a casual visitor, but the sky shows are stunning. If you go, splurge on a theater package to see a couple of them.

Adler Planetarium

Courtesy of City of Chicago

American Girl Place The mecca for young girls anchors Water Tower Place along the Magnificent Mile. Shoppers find historical- and modern-theme dolls and clothing, plus a bookstore and cafe.

American Writers Museum Tap away on a typewriter, play word games or spin the Wheel of Emotions as you explore writers and writing at this new museum just north of Millennium Park.

Andy’s Jazz Club This River North spot stands out for its 41-year history of live music and for dinners of braised short rib and rack of lamb.

The Art Institute of Chicago The Modern Wing showcases 20th- and 21st-century art. The renovated older galleries span 5,000 years and include some of the world’s major works of art. The museum’s website provides downloadable mini tours.

Bobby’s Bike Hike Guided biking or walking tours detail Chicago history.

Buckingham Fountain In Grant Park, one of the world’s largest fountains jets into action for 20-minute shows on the hour from 9 a.m. to 10 p.m. and a finale at 10:35 p.m.

Buckingham Fountain

Buckingham Fountain

Chicago Architecture Foundation River Cruise Entertaining 90-minute history lessons—covering the details of more than 50 buildings—are held on the decks of Chicago’s First Lady boats.

River cruise

Photo courtesy of Choose Chicago/Adam Alexander Photography

Chicago CityPASS See five attractions—the Shedd Aquarium; The Field Museum; The Ledge at Skydeck Chicago; 360 Chicago or Museum of Science and Industry; and the Adler Planetarium or the Art Institute—for about half the cost of the total for individual admissions.

Chicago Helicopter Experience Riders soar over the sprawling parks lining Lake Michigan and past glass-encased skyscrapers.

Chicago Riverwalk A new pedestrian-friendly trail— part of a multi-decade river revitalization plan—runs 1 1⁄4 miles along the river from Lake Michigan west to Lake Street. Explore floating gardens, public art, waterfront restaurants, and outfitters with boats, bikes and water taxis.

Chicago Riverwalk

Chicago Riverwalk

Festivals Chicago knows how to throw a party. Some summer highlights: barbecue and bands at Windy City Smokeout, the music festival Lollapalooza, and Chicago Air and Water Show.

The Field Museum This treasure trove of science and anthropology is a Midwest must-see, if only to meet Sue, the resident T. rex. Thanks to reciprocity agreements, you might score free admission if you show a membership card from another science museum.

Frank Lloyd Wright Trust tours Learn about Wright’s architectural legacy in the Chicago area—including his Oak Park home and studio, Unity Temple and the Robie House—on guided tours.

Garfield Park Conservatory The 1908 building shelters 10,000 plant varieties beneath a 2.8-acre glass dome. Free programs include yoga sessions.

Hot Tix Get last-minute, half-price tickets to direct-from-Broadway shows and other productions at two downtown locations or online.

John G. Shedd Aquarium See beluga whales and other Pacific Northwest coast creatures at the Abbott Oceanarium exhibit and at aquatic shows. 

Shedd Aquarium

Shedd Aquarium

360 Chicago The five-state view from the 94th floor is spectacular and worth admission on a clear day.

The Ledge at Skydeck Chicago Step out 1,353 feet above the ground in a glass box that juts 4 feet out from Willis Tower, the city's tallest building.

The Ledge at Skydeck Chicago

The Ledge at Skydeck Chicago

Lincoln Park Zoo Opened in 1868, the free zoo is one of the nation’s oldest. More than 200 species live on the 49 acres. Favorite stops include the penguin cove.

The Magnificent Mile More than 460 high-end stores, including boutiques, department stores and high-rise shopping malls, line North Michigan Avenue.

Millennium Park Crowds gather to photograph the Cloud Gate sculpture as well as for concerts (many free) at Jay Pritzker Pavilion.

Millennium Park

Millennium Park

Museum of Contemporary Art Chicago A light-filled venue in the Streeterville neighborhood displays four stories of mod works from the 1920s to the present.

Museum of Science and Industry Visitors love programs about technology, transportation and more. The exhibit You! The Experience ages your face 30 years within minutes and makes a giant heart beat in time with your pulse.

Navy Pier The city’s most popular attraction draws crowds with the 200-foot- tall Centennial Wheel, the Chicago Children’s Museum, restaurants, shops, Imax movies and boat rides.

Oak Street Beach Potted palm trees, a life-size chess set and access to the 18-mile Lakefront Trail make this urban beach a must.

The Second City A training ground for big-name comics, the theater stages shows that skewer current events.

Wrigley Field The Chicago Cubs play their 103rd season at Wrigley this year. A new entertainment park with a large video board is part of an ongoing $900 million project to upgrade the field, as well as develop the surrounding area.

Where to eat

The Angry Crab No plates, no silverware, just giant bags of succulent shellfish coated in lemon pepper, garlic butter or Angry Cajun spices. Dine at either the Wicker Park or Rogers Park location.

The Bongo Room The funky Wicker Park cafe is known for great breakfast dishes, fist-thick breakfast burritos and hotcakes with seasonal fruits and fillings.

Buddy Guy's Legends Soul food and live music restore weary travelers.

Carnitas Uruapan Freshly made corn tortillas cradle pork that’s slow-cooked until golden and tender. Try with chicharrons (fried pork rinds) at this Pilsen spot.

Duck Duck Goat Top Chef winner Stephanie Izard’s playful take on a Chinese restaurant delivers a fun evening in the West Loop. Fare such as soup dumplings and spring rolls comes on blue porcelain plates decorated with goats.

Eataly Think of this place as a multistory celebration of Italian edibles. Counter service stations offer fresh hand-filled cannoli; Osteria di Eataly serves house-made pastas and classic Negronis; and aisles stock imported olive oils and antipasti for home cooking.

Elske Danish-American fare might include sturgeon with trumpet mushrooms or squash fritters with trout roe at the West Loop restaurant. Candles atop wooden tables cast a welcoming glow.

Frontera Grill Celeb chef Rick Bayless owns the James Beard Award-winning restaurant specializing in seasonal Mexican flavors in River North. The homemade mole sauce always draws raves, as do the margaritas.

Lou Malnati's Pizzeria Of all the deep-dish joints in the city, many locals swear this chaiin (with 45 Chicagoland locations) serves the best.

The Gage Top-notch whiskey and beer pair with meals like the Gage venison burger, with smoked Gouda and pickled onions, at a pub near Millennium Park.

Mercat a la Planxa Catalan-inspired tapas star on the seasonal menu in the fine-dining restaurant adjacent to the Renaissance Blackstone Hotel in the South Loop.

Mindy's HotChocolate Order seasonal desserts with any of 11 varieties of rich hot chocolate topped with house-made marshmallows in Bucktown/Wicker Park.

Nutella Cafe The silky-smooth hazelnut spread stars in crepes, croissants, gelato, waffles and more at the new North Michigan Avenue spot. Nutella Cafe on Facebook

Oiistar Get your ramen fix in Wicker Park. A bowl of broth swims with fresh noodles, pork belly, egg and garlic. Also delicious: buns stuffed with duck.



Pizzeria Uno The deep-dish pizza craze began at this little River North spot. Pies feature crispy-edged crust, gooey cheese, toppings and a chunky tomato sauce.

The Purple Pig Snagging a spot at one of the communal tables may take an hour at this downtown spot, but patience pays off. Linger over small plates like the milk-braised pork.

Revival Food Hall Grab food to go from one (or more) of 15 stalls featuring Chicago favorites like Black Dog Gelato and Furious Spoon. The 24,000-square-foot marketplace sits on the ground floor of The National, a 1907 building in The Loop.

Smyth and the Loyalist Chefs in the open kitchen prepare inventive five-, eight- and 12-course meals for guests in Smyth’s brick-walled fine-dining space in the West Loop. Downstairs, The Loyalist serves craft cocktails, a terrific cheeseburger and fare like chicken liver mousse.

Spinning J Retro furniture surrounds the vintage centerpiece: a 1928 soda fountain, where Humboldt Park diners order handmade sodas, pot pies, breakfast sandwiches, Thai tea milk shakes and s’mores pie.

Stan’s Donuts and Coffee The double-chocolate old-fashioned doughnut is decadent on its own but even better sliced with a thin layer of fresh gelato in the middle.

Terzo Piano The menu of the dining option at the Art Institute of Chicago stars Mediterranean-inspired dishes, such as lamb Bolognese.

Topolobampo A sleek Mexican restaurant owned by chef Rick Bayless connects to his Frontera Grill in River North and serves organic and heirloom produce.

Where to stay

Ace Hotel Chicago Some rooms come with turntables or guitars in this industrial-chic West Loop hotel created in a building that once housed an Italian-American cheese- making company. Rooftop lounge Waydown hosts nightly live music.

The Blackstone Hotel Spend a bit to get a room or suite with a view of Lake Michigan at this South Michigan Avenue hotel that has hosted 12 presidents.

Chicago Athletic Association Hotel A boutique rehab at this historical men’s sports club added six bars and restaurants with 241 cushy guest rooms above Michigan Avenue. In the Game Room bar, fair-themed bites accompany shuffleboard, chess, bocce and billiards.

Freehand Hostel Aimed at social travelers, room options include a shared dorm with bunk beds, the lobby sports a craft cocktail bar, and staff will arrange activities like cooking classes and parties.

Freehand Hostel

Photo courtesy of Freehand Chicago/Adrian Gaut

The Godfrey Hotel An ultramodern elliptical lobby and fourth-floor lounge with retractable roof and two-level fire pit set a luxurious tone in the 221-room hotel.

Holiday Inn Chicago Mart Plaza At the affordable chain hotel in River North, every room has a view and free Wi-Fi, and a skywalk connects to the Merchandise Mart.

Hotel EMC2 Tuxedoed robots Leo and Cleo might bring shampoo or towels to your room at this new Streeterville hotel, where science and art elevate the guest experience. A mural and a collection of vintage books serve as a backdrop to contemporary American cuisine in the on-site Albert restaurant.

Hyatt Place Chicago/River North Hotel Breakfast is included with an affordable stay at a prime location.

Kimpton Hotel Allegro Touches of shimmering fabric echo original Art Deco design in this theater district landmark. In-room spa services help you relax.

Kinzie Hotel Chicago maps serve as murals in the 215 guest rooms and suites, reflecting the River North hotel’s focus on celebrating local art and culture.

Hotel Felix The River North hotel combines a 1927 Beaux Arts building with contemporary furnishings. Sensors reduce energy usage when rooms are unoccupied.

Hotel Chicago The high-energy, upscale hotel with a nightclub just off the lobby stands alongside the House of Blues in Marina City.

JW Marriott Chicago A $396 million project has transformed a historical Burnham building into a luxe hotel. The property includes a 20,000-square-foot spa.

LondonHouse Chicago The 452-room luxury hotel occupies a 1923 former office building in a prime location on North Michigan Avenue. A tri-level rooftop bar overlooks the Chicago River.

The Virgin Hotel Ergonomic headboards support you while sitting in bed, a retro cool Smeg fridge houses the mini bar, and a smartphone app lets you adjust the heat and order room service.

Warwick-Allerton Chicago Beyond its 1920s redbrick Renaissance exterior, the Allerton is contemporary. Rooms at this Magnificent Mile spot are comfortable with calming aesthetics.

The Wit Check-in includes a warm chocolate chip cookie, and throughout the hallways, you’ll hear the chirping of birds and crickets. In the Loop’s theater district.

More information: Choose Chicago


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