Cherry Circle Room is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

1. Cherry Circle Room

8.9
12 S Michigan Ave (at E Madison St), Chicago, IL
American Restaurant · The Loop · 45 tips and reviews

Lucille F.Lucille Fisher: Very retro-as in Don Draper & his crew may come any moment. Beautifully restored, like the rest of the Chicago Athletic Association.Breakfast,lunch, dinner. Great for date nights. Eclectic menu.

Ariana V.Ariana Voyer: Ordered the beef tartare with gouda (wow!), duck entree, brussel sprouts slaw & chocolate mint dessert (yum!). If you sit at the bar, trust the bartender to make something for you. Great mixologists!

Redeye ChicagoRedeye Chicago: The lack of windows, huge curved wooden bar, slick tufted booths and symbols emblazoned on everything feel like Don Draper’s supper club meets illuminati secret society. Read more.

Prime & Provisions is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

2. Prime & Provisions

8.7
222 North LaSalle Street, Chicago, IL
Steakhouse · The Loop · 37 tips and reviews

Amanda C.Amanda Cooper: Get the bacon, you'll thank me later! The shrimp are impressively large and my petite filet was perfectly cooked! Power lunch and date night dining!

Diego R.Diego Reynoso: Great food everything from the steaks to the incredible smores desert (a must do)

Redeye ChicagoRedeye Chicago: A steakhouse’s reason for being is typically the beef. But what you really want is the fried chicken. The crust glinted with salt and was adorned with candied orange zest and flecks of rosemary. Read more.

Italian Village is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

3. Italian Village

8.0
71 W Monroe St (btwn Dearborn St & Clark St), Chicago, IL
Italian Restaurant · The Loop · 86 tips and reviews

Eddy G.Eddy Gonzalez: Great date spot, lasagna was real filling and their pizza feeds 2.

AlisonAlison: Romantic atmosphere and great food

Jessica E.Jessica Estorga: The best pasta & lasagna we've ever had! Beautiful scenery ♥

The Dearborn is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

4. The Dearborn

8.8
145 N Dearborn St (Randolph And Dearborn), Chicago, IL
Gastropub · The Loop · 50 tips and reviews

Dana D.Dana Danielle: Went for drinks! Good spot for client outings in the loop! The long bar at the front with leather seats set an intimate atmosphere.Did not try food but looking forward to!

Christopher F.Christopher Floss: A great new #chicago #restaurant in the #loop at Dearborn and Randolph. Fun atmosphere and unique menu. A must try--for dining or for cocktails after work.

Lori W.Lori W: Mezze plate, burrata salad, and atmosphere

Acanto is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

5. Acanto

8.2
18 S Michigan Ave, Chicago, IL
Italian Restaurant · The Loop · 27 tips and reviews

Raed M.Raed Mansour: Unbelievably pretentious. Seriously overpriced, small and seems more like a Loop businessman's dating spot after work. Thankfully had one drink and moved on.

Chicago TribuneChicago Tribune: You can enjoy budget-friendly pizzas here, as well as some house made pastas. Try the toothsome duck egg spaghetti with creamy pork sugo and grated caciocavallo cheese, a sinfully rich indulgence. Read more.

Kevin M.Kevin M. McNally, CMP: Simply shared, tasty food offerings at a value price and served via a friendly staff. You must try the Risotto; the flavor cooked perfectly. Applause-Applause for this restaurant.

Remington's is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

6. Remington's

8.4
20 N Michigan Ave, Chicago, IL
American Restaurant · The Loop · 28 tips and reviews

Josh S.Josh Scianna: Good date spot, their ceviche is a must-have.

MuratMurat: Close to park, in a lively area. Food is delicious. Crab cake is exceptional. Outdoor seating is available in good weather. Staff is extremely nice, kind and welcoming. Always a line, waiting is short

Pebes J.Pebes Jimenez: Awesome music selection!

Cadillac Palace Theatre is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

7. Cadillac Palace Theatre

9.3
151 W Randolph St (at LaSalle St), Chicago, IL
Theater · The Loop · 66 tips and reviews

Lucille F.Lucille Fisher: Just saw Beautiful, Carol King play. Excellent and the theatre is beautiful, intimate & with a excellent acoustics.

vanessa b.vanessa buenrostro: Very beautiful theatre to check out. The broadway shows, concerts are amazing there with even an awesome view from the balcony.

KristinaKristina: Respect the theater, dress up!

CIBC Theatre is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

8. CIBC Theatre

8.8
18 W Monroe St (btwn S State St & S Dearborn St), Chicago, IL
Theater · The Loop · 33 tips and reviews

Mames R.Mames Ryan: Such a more intimate venue. Only drawback--wait for Ladies' room, but they extended intermission for the misses.

Mike D.Mike Davis: Hamilton! Nice theater.

Deborah V.Deborah Van Der Harst: Seeing Book of Mormon

Cindy's is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

9. Cindy's

8.8
12 S Michigan Ave (btwn E Madison & E Monroe St), Chicago, IL
New American Restaurant · The Loop · 144 tips and reviews

Kindall H.Kindall H: Chic atmosphere welcoming everyone at any age. The food is simple yet superb and the cocktail menu is simple yet sofisticado. Not to mention the spectacular view at this rooftop.

PureWowPureWow: Cindy’s at the CAA is open till the wee hours all week, and it has wild-Michigan-blueberry tarts topped with vanilla crème fraîche and almond streusel.

ChicagoistChicagoist: This rooftop bar atop the Chicago Athletic Association hotel boasts incredible cocktails, a gorgeous design and a view of Millennium Park unmatched by any other bar in Chicago. Read more.

Game Room is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

10. Game Room

8.8
12 S Michigan Ave (at E Madison St.), Chicago, IL
Bar · The Loop · 33 tips and reviews

JonahJonah: This place is awesome!! Huge space with great games like foosball, pool, mini shuffle-board and full scale bocce ball. Fantastic place to go with friends or even a date.

Heather B.Heather Bell: A hidden gem! There isn't a sign with the name. Inside is amazing. It's huge. It looks like a hogwarts style bar. With games. Bocce was awesome but a long wait. Fish tacos were on point. 😋

Sharon T.Sharon Tsao: hidden gem for classy people. Reminds me of the Ace Hotel NYC.

Goodman Theatre is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

11. Goodman Theatre

8.8
170 N Dearborn St (at Randolph St), Chicago, IL
Theater · The Loop · 60 tips and reviews

Kevin D.Kevin Dulin: Very nice and modern intimate theatre. Very fairly priced concessions. Brigadoon was a very good play.

Aaron H.Aaron Holland: Come see A Christmas Carol!

Jessica S.Jessica Stopak: See Red. It's a life changer!

Symphony Center (Chicago Symphony Orchestra) is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

12. Symphony Center (Chicago Symphony Orchestra)

9.5
220 S Michigan Ave (btwn Adams & Jackson), Chicago, IL
Concert Hall · Chicago Loop, IL · 35 tips and reviews

Vivian R.Vivian Ramirez: Best student tickets seating I've ever experienced. Small intimate feel for a symphony space.

ChicagoistChicagoist: The Chicago Symphony Orchestra’s home is one of the most acoustically perfect venues in town and sounds pitch-perfect across a range of musical styles. Read more.

Robert L.Robert LaRue: Come an hour early to hear some background about the pieces. Schmooze with your fellow socialites. You know you want to...

The Gage is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

13. The Gage

8.9
24 S Michigan Ave (btwn Monroe & Madison St.), Chicago, IL
Gastropub · The Loop · 341 tips and reviews

Benjamin L.Benjamin Lodi: Excellent food, great beer selection, and flawless service. Allergy-friendly too! Would be a great choice for date night or a special dinner.

Time Out ChicagoTime Out Chicago: The whiskey list is lengthy and beer options go beyond the basics. The food is rich and flavorful, from the Scotch egg to the Gage burger with melted onion marmalade and gobs of Midwestern Camembert. Read more.

Teri G.Teri Gidwitz: Try the Regular burger - maybe the best burger in the city. Read more.

LH Rooftop is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

14. LH Rooftop

8.6
85 E Wacker Dr, Chicago, IL
Hotel Bar · The Loop · 24 tips and reviews

Holger S.Holger Sommer: Super cool Rooftop Bar. We enjoyed our stay a lot. Will be back for sure.

Jonathan L.Jonathan Levy: Best rooftop in town 🙌🏻

Faisal S.Faisal Sg: Best rooftop view in the whole town 👍🏼

Chicago Riverwalk is one of The 15 Best Places That Are Good for Dates in The Loop, Chicago.

15. Chicago Riverwalk

9.5
Chicago River, Chicago, IL
Waterfront · The Loop · 139 tips and reviews

Lupe G.Lupe Guerra: First walked it on a date in h.s. & found it super romantic & beautiful. Now its great people watching & a serene sit to take in our city

Angelina S.Angelina S.: Romantic walk late at night.💕

MuratMurat: No1 thing t see and do. So lovely and lively, especially in summer. There are many cafes facing river, green areas for peaceful sunbathing, and river tour points. Perfect for people watching.