Collected by Katie Zegar
233 S Wacker Dr, Chicago, IL 60606, USA
Willis Tower—originally known as the Sears Tower—was the world's tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its "bundled...
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...
3908 N Sheridan Rd, Chicago, IL 60613, USA
Chicago is known for its deep dish Chicago style pizza, this however is not what you'll sink your teeth in at Pizza Rustica. Pizza Rustica serves a square thin northern style Italian pizza and they do it well! However they also serve many other...
House on the Rock, Wyoming, WI 53588, USA
A 14-room house that’s now a museum designed and curated by Alex Jordan to house his vast and interesting collections of stuff, it’s easy to spend a whole day in the House on the Rock and never even get to the rest of the 200 acres...
Picnic Rd, Herod, IL 62947, USA
Get everyone outdoors and spend a day hiking, climbing and picnicking in one of Illinois’ most beautiful parks. Garden of the Gods is part of the Shawnee National Forest and has 5.5 miles of interconnected trailways meandering around beautiful...
809 W Randolph St, Chicago, IL 60607, USA
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...
800 W Randolph St, Chicago, IL 60607, USA
Why the best burger in Chicago is served at a bar with a French name might be a question for the ages. But rather than question it, just go there! The single burger at Au Cheval is actually a double, and don't even ask about the double...
2900 W Belmont Ave, Chicago, IL 60618, USA
Back in 2010 Lady Gaga tweeted that she loved the burgers at Kuma’s Corner and today there are still waiting lines out the door just to have lunch. You think that’s the Gaga or the burger? I know that we waited for a good hour to get a table at...
2148 N Milwaukee Ave, Chicago, IL 60647, USA
50 W Randolph St, Chicago, IL 60601, USA
A perfect buttermilk old fashioned donut is fresh and hot with crispy crunchy edges underneath a melting sugary glazy and the minute I’ve eaten one, I’m already dreaming about the next one. Do-Rite hits all these marks with room to spare, which...
820 W Randolph St, Chicago, IL 60607, USA
Stephanie Izard puts together a great restaurant. The Girl and the Goat has been hard to get into since it opened and Little Goat had a 90 minute wait when we went last month. 90 minutes for diner food! That's impressive. Other things that were...
1462 N Milwaukee Ave, Chicago, IL 60622, USA
The “Back to the Future” Delorean in the window is your first indication that this place is awesome. I mean, it has a flux capacitor! Just like it should. If that’s not enough for you, here are a couple more reasons to visit the...
5236 N Clark St, Chicago, IL 60640, USA
Up in Andersonville Svea has served genuine Swedish sausages, meatballs and pancakes in giant portions for decades surrounded by exactly the same blue and gold decor. They don't have a website, they're cash only and you'll definitely have to wait...
1545 N Damen Ave, Chicago, IL 60622, USA
Brought to you by the guys who own Big Star Tacos down the street, Dove’s Luncheonette channels the spirit of a retro lunch counter and the soul of Southern-Mexican fusion food. The menu includes Mexican classics like chili rellenos and...
5022 N Clark St, Chicago, IL 60640, USA
Bongo Room offers one of Chicago’s best brunches at three different locations in the city. I’m partial to the vegetarian croissant served with spinach, tomato and basil mayo on a gigantic croissant. However, if sweet treats are your breakfast...
955 W Fulton Market, Chicago, IL 60607, USA
At visionary chef Grant Achatz’s bar, vessels such as “the Porthole” (pictured) are as original as the drinks. The chef-trained bartenders use fresh herbs, small-batch spirits, and hand-carved ice in their cutting-edge libations....
840 W Randolph St, Chicago, IL 60607, USA
I'm sure anything you get at this swank bar in the heart of the West Randolph restaurant loop is worth it but this bone marrow did NOT disappoint! Smooth and just salty enough with a touch of sweetness from the jam and the heartiness of the toast,...
3201 W Armitage Ave, Chicago, IL 60647, USA
Scofflaw breaks all the craft-cocktail-bar rules by serving strong, affordable drinks that arrive quickly with no snooty attitude. There's even street parking, something anyone driving in Chicago will appreciate. I’m not sure what else you...
4530 N Lincoln Ave, Chicago, IL 60625, USA
This is how your table looks after a night at The Grafton with the mostly empty glasses and a water carafe that’s been filled and emptied at least four times. Not pictured are the hollows you left in the seats from sitting there for 6...
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...
954 W Fulton Market, Chicago, IL 60607, USA
I was tempted to come here by the name here alone. Then I realized its location in Fulton Market is across from The Aviary. LSC and Fulton Market remind me of the Meatpacking District without the pretension. The pisco sours are the perfect mix of...
2900 N Lincoln Ave, Chicago, IL 60657, USA
Started in Chicago in 2009, and slowly making its way throughout the U.S., Bottle & Bottega is hands down one of the coolest and unique new ideas to arrive in the Windy City. Founded by two enterprising young women who ditched the corporate gig to...
77 E Adams St, Chicago, IL 60603, USA
Russia isn’t the first place that springs to mind when I think of tea but despite my ignorance Russian Tea Time offers a fantastic afternoon tea service. This elegant restaurant offer all the things I’d expect for an afternoon tea like scones with...
2139 S China Pl, Chicago, IL 60616, USA
If you want to get bubble tea in Chicago’s Chinatown, go to Joy Yee’s. As you can see, the menu is gigantic and colorful and has so many options you could deliberate for hours. The bubble tea comes with green tea or black tea, lychee jelly, grass...
1215 IN-49, Porter, IN 46304, USA
Just a 45-minute drive from the Chicago’s downtown Loop, 200 foot sand dunes tower over the wild untrammeled shores of Lake Michigan. The Indiana Dunes State Park has 2,000+ acres of wilderness crisscrossed with hiking trails and camping spots and...
2548 N Halsted St, Chicago, IL 60614, USA
Playing live blues music until 4am every night of the week, featuring all of Chicago’s talented local musicians and now newly renovated to take up 3 storefronts on Halstead, Kingston Mines is one of Chicago’s best bars. Go for the 3...
4802 N Broadway, Chicago, IL 60640, USA
Open and thriving since 1907, the Green Mill Cocktail Lounge survived both prohibition and ownership by Al Capone in the 20’s. That alone should make you want to visit. Additionally, the plush restored interior hearkens back to its speakeasy roots...
5153 N Ashland Ave, Chicago, IL 60640, USA
At 10:30pm every Friday and Saturday a line of people form at the corner of Ashland and Foster waiting for entrance into the 11:30pm Neo-Futurist show, a different play every week. With ticket prices dependent on a dice roll, new fresh...
2391 N Stockton Dr, Chicago, IL 60614, USA
Lincoln Park is a wonderful green area nearing Lake Michigan in Chicago. It has a Zoo free to the public as well as green lawns and flower beds. Near the North end is the multiple room conservator. Like the rest if the park it is open free to the...
Collinsville, IL, USA
This 2,200-acre historic site was formerly the city of Cahokia. It’s the largest archaeological site related to the Mississippian culture and one of the largest earthen constructions in the Americas north of Mexico. Cahokia was inhabited from...
1854 W North Ave, Chicago, IL 60622, USA
Quimby’s says they specialize in “unusual publications, aberrant periodicals, saucy comic booklets and assorted fancies” and if that description doesn’t grab you, then this isn’t your kind of place. However, if this is your kind of place then you...
1960 N Western Ave, Chicago, IL 60647, USA
Old school ice cream parlor and soda shop with homemade candy and ice cream since 1921 in the same location in Bucktown. I wish the little jukeboxes on the tables worked but clearly it’s not hampering their business as there’s a line out the door...
4th St SW & Independence Ave SW, Washington, DC 20560, USA
During three years of living in Washington, D.C., I made it my mission to visit as many museums as I could, and the National Museum of the American Indian quickly won me over. I was greeted by a live dance performance and welcomed into a circular...
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