Travel + Leisure is exploring America one three-day weekend at a time. Here’s what to do on a short trip to the Windy City.

By John Scarpinato
August 24, 2016
Getty Images/Universal Images Group

Chicago’s rich history, vibrant food scene, and gorgeous architecture are a major draw for tourists year after year. Each neighborhood offers its own unique feel, particularly the Loop, where most of the action happens—it’s full of restaurants, bars, and other attractions. While the crowds can be overwhelming, the area is a great home base for a short vacation in the Windy City. 

Day One

If you’re arriving by air, you already know that there are two airports that serve the Chicago area (O’Hare and Midway). Both are a bit of a trek from the city’s inner loop, but each is accessible by taxi and public transportation.

Once downtown, check in and drop your bags off at the Chicago Athletic Association before grabbing an afternoon drink at Cindy’s, the hotel’s rooftop restaurant and terrace­. The views of Millennium Park and Lake Michigan are some of the best in the city.

Related: Things to do in Chicago

Speaking of Millennium Park, you should take a stroll through the city’s 25-acre gem while you’re right across the street. In the warmer months, you’ll find dozens of events, concerts, and programs to enjoy. The Bean, which draws tourists from all over the world, is at the center of the park and offers a mirror-like reflection of the skyline. You’ll notice rather quickly that it’s a haven for selfies. Additionally, the Crown Fountain, a shallow reflecting pool near the Bean, provides a refreshing relief from the heat.

If you prefer to cool off in air conditioning, head south on Michigan Avenue to the Art Institute of Chicago. As the city’s top art museum, you’ll find hundreds of contemporary, ancient, and photographic pieces throughout multiple buildings. It’s not an exaggeration to say that you could spend the whole day there and not see everything, so grab a map and pick a few collections to focus on.

Since you're in Chicago, deep-dish pizza is a must for dinner. My personal favorite is Lou Malnati’s, but you can’t go wrong with Pequod’s, Giordano’s, the Art of Pizza, and Gino’s East as well. 

At night, head to Headquarters Beercade, a throwback arcade, with craft beer and some of the best old-school video games. Sluggers, in Wrigleyville, is another spot to relive your childhood. The bar has batting cages, skee-ball, air hockey, and a slew of other games.

Day Two

Start your day with an architecture boat tour on Chicago’s First Lady cruises. It’s a great way to see the city by water and is hosted by the Chicago Architecture Foundation. You’ll learn about some of Chicago’s most iconic buildings and find out how the city went from a small settlement in the 1800s to one of the largest cities in the world.

Aside from Millennium Park, the most popular green space in the city is Lincoln Park. There’s everything from baseball fields, miniature golf, and a driving range to weekly farmers markets and the zoo. Across Lake Shore Drive, you’ll find the North Avenue Beach. Bring a swimsuit to take a dip in Lake Michigan.

If you’re lucky enough to be in town at the same time as the Chicago Cubs, a trip to Wrigley Field is a must. If you can’t snag tickets to a game, hop into one of the many bars in Wrigleyville and watch the game on television while listening to the crowd react outside.

Chicago's other most classic food is the Italian beef sandwich. Al’s #1 Italian Beef claims to have been the first, and they’re still serving a crazy good sandwich. There are multiple locations in the city, so pick one and order an Italian beef with fresh cut fries.

As the day winds down, head to Navy Pier and stake out a spot for the bi-weekly fireworks show. Each is synced with music and can be viewed from the dock or aboard a number of evening fireworks cruises. Shows occur on Wednesdays and Saturdays during the summer between Memorial Day and Labor Day.

After fireworks, enjoy a few drinks in the sky. Streeterville Social sits atop the Loews Chicago Hotel and has 9,000 square feet of outdoor space. You’ll find lounge seating, lawn games, and amazing views of the lake and city. Another popular rooftop bar is J. Parker. It's located above the Hotel Lincoln in Old Town and has delicious cocktails, hundreds of outdoor seats, and small plates from chef Paul Virant.

Day Three

No trip to Chicago would be complete without a walk down Michigan Ave. The “Magnificent Mile” is filled with upscale boutiques, stores, and dining options—plus the architecture and views of the Chicago River are hard to beat. Stop in the Purple Pig for small plates and house-cured meats, or opt for southern classics at Bandera

After some shopping and lunch, head south to “Museum Row," where the Field Museum, Shedd Aquarium, and Adler Planetarium are all within walking distance. Depending on what you're in the mood for, you'll find archeology and history at the Field Museum; multi-colored fish and penguins at Shedd Aquarium; and telescopes, stars, and some of the best views of Chicago’s skyline at the Adler Planetarium.

For lunch, keep it casual with a hot dog, burger, or beef sandwich from Portillo’s. The chain is insanely popular with locals and has locations scattered throughout the city. 

On your last night in the city, choose from two Chicago staples: comedy and the blues. Both have a rich history in the city and there are multiple venues with stellar shows. For jazz, head to Kingston Mines. Tickets range from $12 to $15, the space is intimate, and acts are quite good. The obvious choice for comedy is Second City, which is known for its famous alumni like Tina Fey, Steve Carell, and Stephen Colbert. However, Improv Olympic is a little less commercial—it's where Amy Poehler, Chris Farley, and Seth Meyers got their start.

Finish your trip at one of Chicago's best bars, the tiki-focused Three Dots and a Dash. Their drinks, served in inventive vessels like treasure chests and totem pole mugs, are delicious but strong, so wash it all down with a few of the shareable snacks. The bar is rowdy, fun, and emblematic of Chicago's laid-back yet wildly creative scene. 

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