Where are you going?
Or, let us surprise youSpin the Globe ®

The Perfect Weekend Trip to Chicago

List View
Map View
It's totally possible to eat well, do some quality shopping, and see all the crucial sights in Chicago over a weekend. Here are some of our favorite things to do to get you started.
Save Place
201 E Randolph St, Chicago, IL 60602, USA
FREE
Every June hundreds of internationally renowned blues musicians rock Chicago for 3 days and 4 nights in the world's largest free blues festival. Did I mention it’s free? 3 solid days of music for free! Food vendors flock to Millennium Park for...
Save Place
401 N Franklin St, Chicago, IL 60654, USA
$$$$
I have two pieces of advice for you regarding the Doughnut Vault: 1. Go early. They open at 8am Tuesday-Friday and 9:30am on Saturdays and if you want a breath of a hope of a chance of getting a doughnut before they sell out, you want to be there...
Save Place
3535 N Clark St, Chicago, IL 60657, USA
One of the first craft beer breweries in Chicago, Goose Island is now owned by Anheuser Busch but I’d still recommend checking it out as part of your Chicago experience. The Goose Island Brewpub in Wrigleyville is smack in the middle of a...
Save Place
1060 W Addison St, Chicago, IL 60613, USA
Steeped in history, loved my many, loathed by some, and sorely in need of a championship, Wrigley Field is a true cornerstone of the always controversial sporting world. No trip to Chicago is complete without a visit to this monument to to...
Save Place
1520 N Damen Ave, Chicago, IL 60622, USA
$$$$
The first rule of the speakeasy is that it can’t be easy to find. The Violet Hour’s door is directly across the street from Big Star. Look for the handle on the wall and the light above it, because the door mural changes frequently and...
Save Place
449 N Clark St, Chicago, IL 60654, USA
$$$$
Rick Bayless opened his upscale Mexican restaurants Frontera Grill and Topolobampo in the late 1980s and then won a litany of James Beard Awards, including Outstanding Restaurant (in 2007 and 2017). He took the top spot in the first season of Top...
Save Place
1850 W Grand Ave, Chicago, IL 60622, USA
The sign says “New Antique Store,” which might seem like a misnomer but is in fact a very accurate description of what Urban Remains offers. They sell reclaimed architectural artifacts from old buildings, mostly in the Chicago area and mostly from...
Save Place
50 W Washington St, Chicago, IL 60602, USA
The second most famous public sculpture in Chicago is 50ft high, made of steel and no one knows what it means. It’s doesn’t even have a proper name so it’s just known as “The Picasso.” Pablo Picasso gifted this untitled sculpture to the city of...
Save Place
10000 Bessie Coleman Dr, Chicago, IL 60666, USA
$$$$
Chicago hot dogs are piled high with onions, tomatoes, peppers, and pickles and look like they’ve been dragged through a garden. Several places around town do a great Chicago dog, including the Wiener Circle in Lincoln Park, the notorious late...
Save Place
1601 N Clark St, Chicago, IL 60614, USA
The Chicago History Museum examines Chicago’s local history as well as its position in the larger scope of American history. The engaging exhibits cover a wide range of subjects such as Abraham Lincoln’s life and presidency, the first locomotive...
Save Place
1300 S Lake Shore Dr, Chicago, IL 60605, USA
It’s difficult to design a museum suitable for both kids and adults, but Adler makes it look easy. Children will love the area known as Planet Explorers, where they can play astronaut with space rovers and rocket-launch simulators, peer...
Save Place
809 W Randolph St, Chicago, IL 60607, USA
$$$$
West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above)....
Save Place
2007 W Churchill St, Chicago, IL 60647, USA
See our full list of Where to Go in 2015. This summer, the 606, Chicago’s answer to New York’s High Line, debuts. The parks and trails on 2.7 miles of repurposed elevated train tracks connect four neighborhoods, bringing green space to places that...
Save Place
Chicago, IL 60601, USA
Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel...
Save Place
2657 N Kedzie Ave, Chicago, IL 60647, USA
$$$$
In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is...
Save Place
5507 N Clark St, Chicago, IL 60640, USA
The goods at Arrin Williams’s year-old Andersonville shop, Haymaker, are mostly handmade by local artisans. Powder-coated-steel side tables by David Greene, hanging plant holders made from reclaimed wood, and coveted leather bags by Chicago-based...
Save Place
141 W Jackson Blvd, Chicago, IL 60604, USA
For their roving, event-based Volume Gallery, Claire Warner and Sam Vintz pluck contemporary American designers like Thaddeus Wolf and Rich Brilliant Willing and set up short-run installations at galleries all over Chicago. One of Chicago’s own,...
Save Place
111 S Michigan Ave, Chicago, IL 60603, USA
$$$$
See our full list of Where to Go in 2015. The Art Institute of Chicago hosts the first exhibition devoted to Britain’s rising-star architect David Adjaye in September. Also in the fall, the world’s leading design talents will gather for the...
Save Place
1200 S Lake Shore Dr, Chicago, IL 60605, USA
$$$$
My three year old was fascinated by the Jellies Exhibit—one of many engaging displays—at the Shedd in Chicago. What a joyful moment, capturing the wonder of a young mind.
Save Place
113 N Green St, Chicago, IL 60607, USA
The skeleton of the new Chicago Soho House once belonged to a belt factory—and though the space has been luxuriously renovated and fit with plush leather chairs, over 250 pieces of art, chandeliers, and beds with Egyptian cotton sheets, the...
Save Place
825 W Fulton Market, Chicago, IL 60607, USA
$$$$
A primo sourcing grounds for picnic provisions or a casual cafe meal, Publican Quality Meats is the latest food enterprise by the never-miss restaurant team behind Avec, Publican, and Big Star. Billed as a contemporary American butcher shop, its...