Whether it’s the skyscrapers and great architecture, art, history, music, or delicious food, there’s so much to do and see in the city if Chicago. If you’ve got just a weekend in Chi-Town, you’ll need an effective itinerary to maximize your stay. So start searching for flights to Chicago and enjoy a whirlwind 48 hours in the Windy City!
Start your day off at the Pittsfield Cafe – an inconspicuous little diner located in the Pittsfield Building. While the diner may be unassuming, the menu, which includes dishes like corned beef hash, eggs any way you like, and pancakes and waffles, has something for everyone and is sure to leave you satisfied.
Next, you can walk off some of that breakfast at the nearby Millenium Park. Make sure to make your way to the Cloud Gate sculpture, known by its more popular name – “the bean.” The sculpture’s design offers a warped reflection of things around it, making it ideal for some surreal looking selfies.
After you’ve finished at the park, head over to the historic John Hancock Observatory, now known as 360 CHICAGO.
Visitors can enjoy an exhilarating view that’s even better than the view from their flights to Chicago, and there’s also plenty of activities for everyone to explore. If you’re traveling with kids, 360 CHICAGO offers activities to keep them entertained.
Be sure not to miss the interactive and panoramic touch screen that teaches you about the city’s history, culture, and famous landmarks with a 360-degree, immersive experience.
Lines are usually long, so go early if you can.
Check out the foodie-friendly River North neighborhood. For a Prohibition-themed experience, check out Prohibit at 116 W Hubbard Street.
Take the subway or cab it to Wrigley Field. This iconic baseball stadium, home to the 2016 World Series-winning Cubs, can even be appreciated from the outside, in case a paid tour doesn’t interest you. Take the chance to have a beer at Murphy’s Bleachers, a legendary sports bar right across the street that’s often a first stop for sports fans landing on flights to Chicago.
As evening comes around, it’s time for a few drinks. Mosie along to Gilt Bar on Kinzie Street – a highly-rated gastropub where you’re sure to have some refreshing drinks.
After you’ve built up a bit of an appetite, head to Lou Malnati’s to have a signature Chicago meal – deep dish pizza! Their buttermilk crust pies with thick sauce and a thin layer of sausage will probably be the most memorable taste of Chicago.
There’s nothing like a few laughs to cap off the evening, so make your way to The Comedy Bar. Offered in the late evening, this show includes some of the future stars of comedy. Tickets are only $20, and you can enjoy some of the Comedy Bar’s standard pub fare as you wait for the next show (locals love their beer brewed in-house!).
Start your day off right at The Original Pancake House, which, as the name states, serves up some pretty delicious pancakes with all kinds of irresistible toppings.
Fashionistas should not miss shopping at the Magnificent Mile! Troll through top brands like Louis Vuitton and Gucci, and check out the indie stores for totally unique styles (Ikram, located close to the Magnificent Mile is a favorite of Michelle Obama’s). For more eclectic stores, check out shops like Sofia on East Oak Street.
Next, head on over to the Museum of Contemporary Art, where you can check out some amazing works of art and sculpture.
As it’s almost lunch time, head to Portillo’s for their legendary Chicago-style hotdogs and Italian beef sandwiches – another Chicago eating experience you shouldn’t miss!
RELATED: Want to throw in a bit of partying to your weekend in the Windy City? Read this guide on Where to Enjoy the Chicago Nightlife!
After lunch, take a river cruise by the Chicago Architecture Foundation on the First Lady. The 90-minute cruises leave from the southeast corner of the Michigan Avenue Bridge at Wacker Drive. You can enjoy views of Chicago’s skyline and a very knowledgeable guide will give you some great insight into some of the city’s earliest buildings.
After your cruise, refresh yourself in the classy vintage vibe at the Beacon Tavern, where the specialty cocktails and small bites are excellent.
Continue drinking at Fado’s Irish Pub, where you’re guaranteed a rollicking good time with a pint of Guinness and a lively crowd that knows how to party!
Make your way to Chinatown to close out the night, and make MingHin Cuisine your first stop. You can enjoy some amazing dumplings and main dishes that offer traditional flavors and hearty portions.
And there you have it – 48 hours in one of the world’s most diverse and unique cities. In the heart of the country, it’s quite easy to find flights to Chicago. So what are you waiting for? Take a weekend trip and relish in the beauty of this cosmopolitan city!