4. Mastro's Steakhouse
8.9
520 N Dearborn St (at Grand Ave), Chicago, IL
Steakhouse · Near North Side · 122 tips and reviews
Rishad Tobaccowala: Dragon Fire Martini is delicious
Matthew Stern: Best of the best in Chicago. Pomeg martini, crab, bone in filet, butter cake! I've done all the work for you!
Time Out Chicago: Try the chef’s cut New York strip from our 100 Best list: The high-end chain had us woozy with its dry-ice martinis, warm butter cake, and expertly cooked and seasoned cuts of beef.
8. Gene & Georgetti
8.9
500 N Franklin St (at W Illinois St), Chicago, IL
Steakhouse · River North · 66 tips and reviews
Epicurious: This "hotspot" (literally!) keeps patrons warm during the winter - its 1,100°F Vulcan broiler sears steaks to perfection with plenty of heat to spare. Sip on icy martinis to keep cool in the summer.
Chicago magazine: Wet-aged steaks still rank among the best in town. On weekends, latch onto first-rate prime rib. The wine list is forgettable, but the well-priced martinis are excellent. Read more.
Seth Putnam: The martini. Always the martini.
Time Out Chicago: You can’t sit among the sparkling fountain and oversized flower arrangements, slowly sipping your perfectly shaken martini, without thinking that your mom was right all along: You are special.
Time Out Chicago: You can’t sit among the sparkling fountain and oversized flower arrangements, slowly sipping your perfectly shaken martini, without thinking that your mom was right all along: You are special.
Claire Watkiss: Definitely worth the experience. Got to choose our own tea blend and a few pastries. Waiter was so sweet and even took a picture of us at the end! Love the space, so historic and unique.
12. Smith & Wollensky
8.3
318 N State St (at Marina City), Chicago, IL
Steakhouse · Near North Side · 103 tips and reviews
Chicago magazine: Order a dry martini and enjoy the terrace until the dining crowd comes in around 6pm.
Nancy R.: Catch a drink on the patio when the sun is out. Great views, total Chicago experience. We were there for a drink and a snack. Martinis were great., Had fries (nit bad). Service outstanding.
Stefanie: Awesome Chicago spot right on the river. Seating outside is best if weather permits. Filet, whipped potatoes and that bread. A last meal wish. I also love the raspberry martini.
José Viruet: Little Rose Martini, simply heaven!
Sarp Erkaya: Trendy spot, friendly service, amazing food! Fillet is cut perfectly and cooked just right. 👏🏼 get the mac&cheese and the corn! Start w oysters and pair it all with a martini! 🍸Perfect dinner 🙌🏼
M S: Filet. Stroganoff. Creamed spinach. Chocolate cream pie. So much yum.