48 Hours in Chicago: The Ultimate Itinerary

Day 1: Morning

10 a.m.: One of the best ways to explore the city is on foot. Visit the Chicago Riverwalk on your first morning to get your bearings as well as a little exercise. The 1.25-mile-long well-maintained path includes four diverse districts: the Confluence, the Arcade, the Civic, and the Esplanade. Listen to free concerts on Sundays, relax in Adirondack chairs toward the east end, view public art, and sample inventive bites and cocktails restaurants like Beat Kitchen on the Riverwalk, Chicago Brewhouse, or City Winery at the Chicago Riverwalk. Enjoy views of the boats and kayaks on the river as well as great people watching and seasonal events like the Riverwalk Fall Festival and Art on theMart.

Noon: To sample and discover new wines in a trendy Lincoln Park setting, visit Verve Wine + Provisions. You’ll find that the staff is full of passionate and knowledgeable wine drinkers, ready to point you in the right direction depending on your tastes and needs. Open Sundays for brunch from 11:30 a.m. until 2:30 p.m., enjoy noshes and nibbles, from salads to pancakes to cheesy grits to burgers. Or expand your horizons and visit during one of the celebrated tastings to try something fresh and exciting. Not only will you learn something new, but you'll also have the opportunity to bring a few bottles of wine home with you so that you can relive the adventure.

Day 1: Afternoon

2 p.m.: Pam Beesly, Dwight Schrute, Michael Scott, and Jim Halpert fans will love exploring Chicago’s newest pop up, The Office Experience. Tickets are on sale now for this immersive adventure, which opened Oct. 15 at The Shops at North Bridge on the Magnificent Mile. See Schrute Farms, take photos in the Dunder Mifflin set, watch Jim and Pam’s romance unfold (again) in a set recreation, and marvel at the show’s costumes and props. Tickets are timed and must be purchased in advance. Afterward you can spend a little time shopping for souvenirs and Chicago keepsakes.  

4 p.m.: A much-needed siesta might be in order at this point in the day, especially as you gear up for a long and fun night out. Check-in at the stylish Neighborhood Hotel, located in Lincoln Park, where you can nap, have a snack in the kitchen, or watch your favorite television show. Choose between one, two, or three-bedroom accommodations, depending on your group’s size, and recharge. This property is like no other and it’s located in a very walkable neighborhood, conducive to wandering and investigating the city.

Day 1: Evening

7 p.m.: Improvisational comedy, as well as sketch and stand-up for that matter, is as essential to Chicago’s storied nightlife as quality tomato sauce is to deep dish pizzas. The Second City first opened in 1959 and has churned out amazing talent including Bill Murray, Eugene Levy, Catherine O’Hara, Tina Fey, and Kate McKinnon, to name just a few. Spend a few hours at the evening shows for a chance to see what all the hubbub is about.

9 p.m.: For a delectable meal to write home about, make a reservation at The Bristol, located in the Bucktown neighborhood, for an eight-course tasting menu with unique global wine pairings. You’ll get an education as you travel from course to course, with a behind-the-scenes look into what inspired the chef to create dishes like Hamachi tartare, heirloom tomato salad, yellow squash gazpacho, and more. Each plate will make your eyebrows raise with curiosity and delight.

11 p.m.: Part of what makes a night in Chicago so magical is a stellar skyline view. Enjoy inventive Instagram-worthy cocktails at Upstairs at the Gwen. This art deco-inspired bright and colorful outdoor space is a bit tucked-in and feels more private than other rooftop bars. When the weather in the city turns and gets a bit chilly, the terrace is still open with firepits and belly-warming drinks and bites. 

Other fantastic rooftop bars with twinkling skyline views, include Cindy’s Rooftop, on top of the Chicago Athletic Association Hotel; Chateau Carbide, on top of Pendry Chicago; and LH Rooftop, on top of LondonHouse Chicago.

Day 2: Morning

10 a.m.: Much like New York City’s High Line park, The 606—created on the old elevated Bloomingdale train line—is a great way to experience the urban outdoors. What was once an abandoned rail line is now a multi-use park and public space used for running, walking dogs, cycling, and picnicking. Walk the entire 2.7-mile length, between Ashland and Ridgeway, or hop off at any one of the 12 access points. Keep your eyes out for the public art along the way: A Greater Perspective, Birds Watching, Children Are Our Future, Graffiti Garden, and Turning Sky.

When you’ve had enough of wandering around outside, grab a slice of deep-dish pizza and weigh in or which pizzeria serves up the best slice—Giordano’s, Lou Malnati’s, Pizzeria Uno, Gino’s East, or Home Run Inn?

Noon: Chicago is well-known for its architecture and one way to see some of the most famous buildings is to take either a guided walking tour or a Chicago River boat tour with the Chicago Architecture Foundation. You’ll be rewarded with an in-depth understanding of Chicago’s history as well as the city’s most modern innovators. Either way, guided or not, plan to see the Willis Tower, 875 North Michigan, Aon Center, Aqua, Tribune Tower, The Wrigley Building, Marina City, Civic Opera House, Merchandise Mart, and Chicago Water Tower.

Day 2: Afternoon

2 p.m.: Chicago has an impressive list of world-class museums, from the Art Institute of Chicago to the Museum of Contemporary Art Chicago to the National Museum of Mexican Art. Chicago’s Museum Campus includes Adler Planetarium, the Shedd Aquarium, and the Field Museum (as well as Soldier Field and McCormick Place). You could spend weeks exploring the joys these museums have to offer but we recommend spending a few hours exploring the expansive collection at the Art Institute. If you're trying to figure out which works to see, curators compiled a list of highlights that can be seen in an hour. If you need a snack, stop the museum's cafe or grab an appetizer from the upscale Terzo Piano restaurant.

Day 2: Evening

4 p.m.: To beat the crowds, plan on visiting one of Chicago’s top tourist attractions, Millennium Park, in the early evening. Right next to the Art Institute, this celebrated public space is home to the Jay Pritzker Pavilion, an outdoor shiny amphitheater with lots of live events; Cloud Gate, aka The Bean; Crown Fountain, an interactive set of art towers; and Lurie Garden. Maggie Daley Park is perfect for those who like a little adventure—you can play minigolf, check out the climbing wall, skate at the ribbon, or play a round of tennis.

8 p.m.: Reserve a table at the much talked about Roka Akor for steak, seafood, and sushi. The Japanese wagyu is a celebrated menu item, as are any dishes cooked on the signature robata grill. Located on Clark Street, in the heart of Chicago’s lively River North neighborhood, you’ll have easy access to post-dinner nightlife.

11 p.m.: After your belly is full, head out to a couple of Chicago’s noteworthy neighborhood bars. Popular bars in River North, all within walking distance to Roka Akor, include Hubbard Inn, which is open until 3 a.m. on Saturdays; The Boss Bar, a late-night old Chicago-style bar with community events; and Arbella, the only hip bar in the city with a cocktail called “I Eat Stickers All The Time.” Each locale offers a distinctive flair.