Chicago Trip Guide | Midwest Living

Chicago Trip Guide

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.

Andy’s Jazz Club This River North spot stands out for its 40-year history of excellent 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 neighborhood biking or walking tours detail Chicago’s history. On the Lakefront Neighborhoods tour, pedal past Gold Coast mansions and the Lincoln Park Zoo.

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. Starting at dusk, lights and music enhance the scene.

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.

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.

Garfield Park Conservatory A 3-acre world of plants under glass offers year-round enjoyment. Free.

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

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

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

Lincoln Park Zoo This North Side zoo often prompts visitors to marvel, “This is free?” A nature boardwalk, the children’s zoo and the carousel are reliably entertaining.

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

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, plus hosts evening jazz concerts during the summer.

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 A new (bigger) Ferris wheel dominates the city’s most popular attraction. Also on site: the Chicago Children’s Museum, Chicago Shakespeare Theater, restaurants, Imax movies and boat cruises.

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 (including Jim Belushi, Mike Myers and Tina Fey), the theater stages smart shows that skewer current events.

Wrigley Field The Chicago Cubs, fresh off their first World Series win since 1908, play their 101st season at Wrigley in 2017. An ongoing $750 million project will restore and expand 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. Dining at either of two locations is worth the mess.

The Boarding House Owned by a master sommelier, the place sparkles under light fixtures made with thousands of wine bottles. An extensive wine list complements entrees like venison loin with mustard greens, bacon and grits.

The Boarding House

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.

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. 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 puttanesca-filled panini and Nutella crepes; Osteria di Eataly serves house-made pastas and classic Negronis; and aisles stock imported olive oils and cheeses for home cooking.

Frontera Grill Celeb chef Rick Bayless owns the James Beard Award-winning restaurant specializing in seasonal Mexican flavors in River North.

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, fried jalapeños, mushrooms and pickled onions, at a gastropub 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.

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


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—layered on in that order.

Primehouse All dry-aged steaks are fantastic at The James Chicago hotel in River North. Try fill-your-own doughnuts for dessert.

The Purple Pig Snagging a spot at one of the communal tables may take an hour, but patience pays off. Linger over small plates (like the milk-braised pork) and a well-curated wine and cheese list.

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.

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

Chicago Athletic Association Hotel A boutique rehab at this historical men's sports club added ive bars and restaurants with cushy guest rooms above Michigan Avenue.

Freehand Hostel Aimed at social travelers, room options include a shared dorm with bunk beds, the lobby sports a craft-cocktail bar, and staff arranges activities like tours 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.

Hard Rock Hotel Chicago Retro-chic decor and free Fender guitar loaners are just two reasons to love this salute to music in the 1929 Carbide and Carbon Building.

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.

Kimpton Hotel Allegro Touches of shimmering fabric echo original Art Deco design in this theater district landmark.

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.

Renaissance Blackstone Hotel Spend a bit to get a room overlooking Lake Michigan at this South Michigan Avenue hotel that has hosted 12 presidents.

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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