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Chicago Restaurants
Gibsons Bar & Steakhouse is one of Chicago Restaurants.

1. Gibsons Bar & Steakhouse

9.0
1028 N Rush St (at E Bellevue Pl), Chicago, IL
Steakhouse · Gold Coast · 282 tips and reviews

Bachelor10Bachelor10: They have six private rooms that can hold groups of any size. Lock one down so the crowds don’t have to hear the Bachelor sobbing when you guys tear him apart. Read more.

David Burke's Primehouse is one of Chicago Restaurants.

2. David Burke's Primehouse

616 N Rush St (at E Ontario St), Chicago, IL
Steakhouse · Near North Side · 124 tips and reviews

Bachelor10Bachelor10: Don’t have time to visit? Grab a brunch box to go on Sunday before you head to the airport. We like the Hangover (Mini Burgers and fries, Mac N’ Cheese with bacon & a Monte Cristo). Read more.

Benny’s Chop House is one of Chicago Restaurants.

3. Benny’s Chop House

444 N Wabash Ave (at E Illinois St), Chicago, IL
Steakhouse · Near North Side · 65 tips and reviews

Bachelor10Bachelor10: Ask if the Cajun tenderloin is available. A special, off-menu order that - when available - is the best thing they have; though if not, you’ll still have plenty to choose from. Read more.

Gene & Georgetti is one of Chicago Restaurants.

4. Gene & Georgetti

8.8
500 N Franklin St (at W Illinois St), Chicago, IL
Steakhouse · River North · 65 tips and reviews

Bachelor10Bachelor10: The portions at Gene & Georgetti’s tend to lean on the “that thing is enormous” side so keep that in mind when ordering. There’s nothing less impressive than toting around a doggy bag at the club. Read more.

The Capital Grille is one of Chicago Restaurants.

5. The Capital Grille

8.8
633 N Saint Clair St, Chicago, IL
American Restaurant · Streeterville · 60 tips and reviews

Bachelor10Bachelor10: If you are going for a Private Room (and you should) ask for The State Room (seats up to 16 rowdy people) over the smaller Board Room. Read more.

Chicago Cut Steakhouse is one of Chicago Restaurants.

6. Chicago Cut Steakhouse

8.8
300 N La Salle Dr (at Carroll Ave), Chicago, IL
Steakhouse · River North · 145 tips and reviews

Bachelor10Bachelor10: Need a power breakfast to kick-start the day? Come here for their insanely thick Breakfast Sandwich or incredible New York Strip & Eggs. And do NOT skip the hash browns. Read more.

Mastro's Steakhouse is one of Chicago Restaurants.

7. Mastro's Steakhouse

8.7
520 N Dearborn St (at Grand Ave), Chicago, IL
Steakhouse · Near North Side · 121 tips and reviews

Bachelor10Bachelor10: If the steep prices have some of the guys scared of going, you can choose to bring your own wine & only pay a $25 corkage fee. We hear the Trader Joe’s Two-Buck Chuck Cab goes great with a $60 porter. Read more.

Keefer's Restaurant is one of Chicago Restaurants.

8. Keefer's Restaurant

20 W Kinzie St (btwn Dearborn St & State St), Chicago, IL
American Restaurant · Near North Side · 42 tips and reviews

Bachelor10Bachelor10: Glenn Keefer is always there to greet people (he is the bald guy hovering around the bar) so say hi and buy the man a drink. Read more.

Ruth's Chris Steak House is one of Chicago Restaurants.

9. Ruth's Chris Steak House

7.8
431 N Dearborn St, Chicago, IL
Steakhouse · Near North Side · 50 tips and reviews

Bachelor10Bachelor10: One key of working with a chain: they are used to booking for big parties. You can go to the Ruth’s Chris web site and contact their Private Dining Manager directly who will hook everything up. Read more.

N9NE Steakhouse is one of Chicago Restaurants.

10. N9NE Steakhouse

440 W Randolph St (at N Canal), Chicago, IL
Steakhouse · West Loop · 41 tips and reviews

Bachelor10Bachelor10: Ghostbar, located on the upper level of N9NE, is a chic ultra-lounge that is a solid option for post-dinner partying. Plan on locking down a booth or table for maximum fun. Read more.