Thursday Night: Chicago

Ah, Thursday night — the only truly social night of the week. It’s the night when babysitters are booked, friends convene, and drinks are imbibed. There are no family obligations to fulfill, no amateurish weekend crowds to elbow through — and the possibilities are endless. The night starts after work and ends whenever you want. In any city. All over the world.

This week, we’re presenting the perfect Thursday night in Chicago, Illinois.


Chicago’s breathtaking skyline. (Photo: Thinkstock)

Somewhere in the middle of America lies Chicago—a bustling city where class and sophistication meets Midwestern simplicity. Its downtown is a hotbed of cultural activity, with art museums, historic architecture, pristine beaches, and world-class restaurants on every block. And with nearly 200 different neighborhoods designed to give you a unique experience, there is literally something for everyone. 

So whether you’re a student at nearby UIC, an out-of-town visitor, or a suburbanite driving in for weekend, here’s how to have the perfect Thursday night in Chi-town. 

5:00 p.m.

As a Chicagoan whom I recently talked to proclaimed enthusiastically, “If you’re not taking advantage of the lakefront in the summer, then you’re an idiot.” Enough said. Start Thursday by taking a stroll down Chicago’s beautiful lakefront. The rippling water, sand, and chill vibe are the perfect way to kick off the night.

Walk along the water, watch the sunset, and unwind with a cold beer at Oak Street Beach Food & Drink. If you like your drinks a little fancy, head to Fig & Olive for one of their signature cocktails. Indulge in a crisp cucumber cosmo while you snack on crostini with crab, heirloom tomatoes, and avocado. Want your drinks with a view? Venture on over to the Godfrey Hotel, whose IO Urban Roofscape provides picturesque views of the southern Chicago skyline. 

Related: Thursday Night: Louisville


Start your Thursday with a signature cocktail at Fig & Olive. (Photo: Fig & Olive)


Sip under the retractable roof at the Godfrey Hotel. (Photo: Godfrey Hotel)

8:00 p.m.

The Second City is a sketch comedy and improv group that boasts successful alumni like Tina Fey, Amy Poehler, Bill Murray, John Belushi, and Steve Carell. Its Thursday night performances begin at 8 p.m. at Up Comedy Club, but be sure to buy your tickets early because they sell out fast. Doors open at 7 p.m., and shows last about two hours. So keep that in mind as you coordinate your dinner plans. 

If you find yourself more musically inclined, Lincoln Hall is the go-to place to hear emerging bands and artists. The venue is beautiful, the staff friendly, and the shows affordable. Tickets start at just $10, with some of the larger shows charging $25. Performances start at 8 p.m. 


Miles Nielsen & the Rusted Hearts perform at Lincoln Hall. (Photo: The Rusted Hearts)

Can’t wait for dinner? Skip the shows and head to Tango Sur in Lakeview. This family-owned business has been a Chicago staple for 20 years, and boasts an extensive wine menu. The Midwest knows how to do steak, and this Argentine steakhouse is no exception. Start with the provoleta before cutting into a juicy rib eye.

Related: Thursday Night: Santa Barbara, Calif.


A cut of meat at Tango Sur steakhouse in Chicago. (Photo: Tango Sur)

10:00 p.m.

If you caught some evening entertainment, you are definitely ready for dinner. Au Cheval has what many call the best burger in Chicago. And you can have it any way you want — with bacon, cheese, and even with a fried egg on top. Wash it down with one of Au Cheval’s specialty beers, like the B. Nektar Zombie Killer.

Nico Osteria on Chicago’s Gold Coast is also a dinner hot spot. Executive chef Paul Kahan is a native Chicagoan and was awarded outstanding chef by the James Beard Foundation in 2013. Take one look at the menu and you can see that he knows a thing or two about Italian seafood. The restaurant features such delicacies as lobster spaghetti, roasted black sea bass, and grilled wild king salmon.  Adding to the ambiance is a large open kitchen, so you can see the cooks prepare your seafood masterpiece.


Try the lobster spaghetti at Nico Osteria (Photo: Nico Osteria)


You’ve had a pretty great night so far, but if you want to go out with a bang, it’s time to go dancing. If house music gets your fist pumping, then Smart Bar is a great choice. With international DJs and a bass-filled sound system, you can dance all night — or at least until the bar closes at 4 a.m. 

Many of us have to work on Friday morning, so if you want a chill nightcap, try the beer garden at Zella. Located in Lincoln Park, Zella serves up a diverse drink menu and plays dance-friendly Top 40 music that will keep you vibing until closing time.


Unwind in Zella’s beer garden. (Photo: Zella/Facebook)

WATCH: Take a tour of downtown Chicago:

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