48 hours in Chicago

Windy City Guide: 48 Hours In Chicago

Chicago is one of the world’s best, underrated cities. Spend 48 hours in Chicago with a little advice and a few tips for a wonderful time.

With so much to do, it’s nice to plan on a leisurely weekend with a few of your favorite things planned. So get ready for your ultimate weekend in Illinois.

48 Hours in Chicago, Illinois

Friday Afternoon

Check into The Gwen in the center of town after touching down. This Luxury Collection hotel offers incredible service, luxurious rooms and a great location. After settling in, put on some comfortable walking shoes and head to Millenium Park to visit Cloud Gate, more affectionately known as “The Bean,” for a photo opp or just a nice sunset view.

Afterward, make your way to The Purple Pig for a tasty Mediterranean meal in a stylish and airy setting. Take to the hotel bar for a nightcap before turning in for a good night’s rest.

Chicago, Illinois


Enjoy a leisurely breakfast at the hotel, then head to The Chicago Institute of Art. Wander the many halls of incredible art and impressive temporary exhibits for a day full of culture and learning. Visit Revival Food Hall for tons of delicious options at lunch. In the afternoon, take a walk down the Magnificent Mile for window shopping or visit the Skydeck Chicago for a blood-pumping experience high above the city.

Make a reservation to one of the city’s hottest new restaurants, Oriole, well in advance. The Michelin-starred fine dining restaurant serves elegantly-planted new American fare. The prix fixe menu includes 12 courses of delicately prepared dishes for a wonderful experience. Visit The Aviary for a drink after dinner.

48 hours in Chicago

Sunday Morning

Sleep in on Sunday morning, then visit Lula Cafe for their delectable brunch. It’s a popular spot, though, so expect a bit of a wait. Order “The Royale,” which is the restaurant’s breakfast sandwich series, for a hearty start to a day of travel. Return to the hotel to check out, then set out for the airport with another great weekend behind you.

48 hours in Chicago

Molly Harris

Molly Harris is a freelance travel journalist dividing her time between the United States and the Western Balkans.

View stories