The Perfect Weekend in Chicago
Collected by AFAR Editors , AFAR Staff
Visitors with only three days in Chicago should maximize their time with ample art and food exposure. Orient yourself by taking an architectural cruise along the Chicago River or get high with a panoramic view of the city from the top of one of its fantastic buildings. Then hit up some of the world-class museums along the lakefront: A visit to the Art Institute, the Field Museum, and the Chicago Architecture Foundation can explain (in a spectacular fashion) the cultural breadth of the Windy City. See the Cubs play ball at Wrigley Field and drink a craft cocktail at one of our favorite bars. In just one long weekend, you'll get a vivid taste of Chicago, a city second to none.
111 S Michigan Ave, Chicago, IL 60603, USA
Wow. The last time I was here was on a high school field trip 35 years ago, and the museum has definitely grown. What an amazing collection—I could have spent days here, but I only had two hours. I followed the museum's suggested top 10, and...
112 E Upper Wacker Dr, Chicago, IL 60601, USA
The Chicago River and Lake Michigan are two of the city’s greatest assets, and there’s no better way to experience both than with an architectural boat tour. While there are plenty of reliable options around, go with First Lady...
111 E Upper Wacker Dr, Chicago, IL 60601, USA
The Chicago Architecture Foundation is a must see if you are an architecture fanatic or just love the Chicago skyline. The CAF has a great shop inside the Historic Santa Fe Building in downtown Chicago. They sell informative books about...
5700 S Lake Shore Dr, Chicago, IL 60637, USA
Anyone who's into model trains should visit the Museum of Science and Industry in Chicago. Originally opened in 1941, The Great Train Story was the largest model train of its day. After being briefly shuttered in 2002 for extensive additions, this...
1060 W Addison St, Chicago, IL 60613, USA
2391 N Stockton Dr, Chicago, IL 60614, USA
7705 N Eastlake Terrace, Chicago, IL 60626, USA
Pick up your morning coffee at one of the many local coffee shops, and walk to Rogers Beach (known by locals as Lighthouse Beach). The sunrise over Lake Michigan is stunning! Locals fish off the lighthouse pier in the early morning semi-darkness....
1520 N Damen Ave, Chicago, IL 60622, USA
The first rule of the speakeasy is that it can’t be easy to find. The Violet Hour’s door is directly across the street from Big Star. Look for the handle on the wall and the light above it, because the door mural changes frequently and...
1035 N Western Ave, Chicago, IL 60622, USA
The Empty Bottle in Ukrainian Village offers great music in a small venue with an angled stage so the views are pretty good from anywhere in the house. The drinks are reasonably priced with friendly bartenders and the location is a bit divey but...
12 S Michigan Ave, Chicago, IL 60603, USA
Forget what you thought you knew about the barhopping experience when you enter through the doors of this blink-and-you-miss-it spot, where just eight coveted seats are available to patrons. That’s because no two bottles are alike in these...
2957 W Diversey Ave, Chicago, IL 60647, USA
It’s easy to span the globe at this Logan Square restaurant, where co-owners Abraham Conlon and Adrienne Lo fuse together flavors from China, India, Southeast Asia, and Portugal in a menu meant for crowds. Do spring for the Arroz...
809 W Randolph St, Chicago, IL 60607, USA
With 24 hours in Chicago, my friend and I headed straight to Girl and the Goat for the food, the drinks and the scene. We didn't have a reservation but after an hour of waiting, people watching, and having fun at the bar the unthinkable happened...
805 S State St, Chicago, IL 60605, USA
As you can imagine, there’s a lot of discussion over who has the best pizza in Chicago; so, here’s what I know for sure: Lou Malnati’s serves a great stuffed pizza, they’re one of the oldest pizza names in town and they have yet to franchise...
177 N Ada St #101, Chicago, IL 60607, USA
Not only do husband-and-wife team John Shields and Karen Urie Shields share an impressive culinary background (one that entails gigs at Tru, Alinea, and Charlie Trotter’s between them), they now share two restaurants: the Loyalist, a...
851 W Randolph St, Chicago, IL 60607, USA
This skin-care sanctuary just opened its doors in Fulton Market’s bustling neighborhood after spending two years in Roscoe Village, where it built an obsessive following for its handmade products. The line was inspired by the...
2780 N Lincoln Ave, Chicago, IL 60614, USA
This Lincoln Park destination, besides being one of the only designer-toy shops in the Midwest, has gained a reputation for being one of the best designer-toy shops in the world. It stocks a wildly diverse selection of vinyl figures and...
19 E Ohio St, Chicago, IL 60611, USA
Walk into the Freehand, a remodeled 1920s dive, and you’ll think it’s a millennial fantasy boutique hotel with its artisanal cocktail and coffee bars, and intensely curated wood-paneled clubhouse lounge filled with leather chairs, blue...
2657 N Kedzie Ave, Chicago, IL 60647, USA
Longman and Eagle is a bar, restaurant, and small inn in the Logan Square neighborhood of Chicago. It's very popular for weekend brunch, and I was charmed by being served a mini beer back with my morning margarita. The food was fantastic: I had...
5219 N Clark St, Chicago, IL 60640, USA
Brimfield specializes in antique glassware, vintage signs, custom upholstered chairs and plaid blankets, pillows and furnishings of every conceivable style and design. The owners began collecting antiques in the UK in the late 1990s and opened...
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