Watch CBS News

Best Double Date Ideas In Chicago

Date night is the time to relax, enjoy the evening and spend time together. Going on a double date night can double the fun; spending time with special friends makes the date night even more memorable.  There are so many excellent double date experiences in Chicago; the difficulty will be deciding which date night experience to do first. Here are the 5 best double date ideas in Chicago.

The Chopping Block
(Photo Credit:

Cooking Class
The Chopping Block
The Merchandise Market Plaza
Suite 107
Chicago, IL 60654
(312) 644-6360

The Chopping Block offers numerous cooking classes that would be great for couples to experience. Classes are intimate and perfect for couples, plus cooking is an excellent way to deepen friendship. Examples of classes offered are sushi making, Steakhouse DIY and Boot Camp, which goes to a deeper level of cooking. There are even wine classes offered. Because they are small, classes do fill up quickly so be sure to plan ahead accordingly. The website offers a printable calendar of classes and individuals can register online.

Paint And Drink
Bottle & Bottega
2900 N. Lincoln Ave.
Chicago, IL 60657
(773) 313-9133

Artistic talent or experience is not necessary to have an enjoyable time at Bottle and Bottega.  Painting and drinking wine are great ways for couples to share in a creative experience, while also having a low cost fun night.  Be sure to check out the calendar of events on the website for the specific details of class offerings.  This particular Bottle and Bottega is BYOB and participants may bring in food items as well.  Bottle and Bottega provides ice, napkins, glasses, wine openers, plastic ware and paper plates.

(Photo Credit:

Pinstripes Chicago
435 East Illinois Street
Chicago, IL 60611
(312) 527-3010

Pinstripes is located in Streeterville, just a block west of Navy Pier on Illinois Street. Pinstripes is a great double-date destination that gets you as far as possible from the monotony of the 'dinner & movie' routine.  Pinstripes offers Italian-American dishes that are made fresh from scratch. Their wood-fired pizzas are just perfect. In addition to a terrific menu, Pinstripes offers bowling and bocce ball.  It doesn't get much better than pizza and bowling for a fun double-date in an upscale location. They also have a wide selection of wines, an excellent selection of craft beers and handcrafted cocktails.

Related: Best Up-And-Coming Chicago Bands To Check Out In 2016

Chicago Architectural River Cruise
224 South Michigan Ave.
Chicago, IL 60604
(312) 922-3432
Location:  Dock is located at the southeast corner of the Michigan Avenue Bridge and Wacker Drive.
Duration:  Total River Cruise takes 90 minutes.

This river cruise is an absolute must for any Chicagoan.  The experience offers a sense of Chicago pride and participants will see the city of Chicago entirely different after taking the cruise.  The tour guides on the River Cruise are all Chicago Architectural Foundation Certified. During the 90 minute cruise, participants will hear the stories of over 50 buildings erected over the past 100 years along the river.  This is a great way to start a fun double-date in downtown Chicago.  Once disembarking the boat, there are hundreds of eating options within walking distance.

FTW Chicago
322 E. Illinois Street
Chicago, Illinois 60611
(312) 881-5000

FTW has over 130 arcade games, a pub grub menu and 32 craft beers available. They also have a huge 105 square foot LCD screen above the bar.
There is a six-hole miniature golf course that takes golfers through the iconic Chicago landmarks such as Water Tower, The Chicago Theater, Wrigley Field and US Cellular Field, Lower Wacker Drive, Art Institute, Museum Campus, and Willis (Sears) Tower.  FTW is a great double-date destination because there is so much to do. It is virtually impossible not to have fun here.

Related: Best Spring Beers In Chicago

Michelle Guilbeau is a writer, reviewer, teacher and business owner. She is also proud founder of, and Michelle enjoys sharing her knowledge of cities, food, travel, education and parenting issues with her readers. Her work can be found on

View CBS News In
CBS News App Open
Chrome Safari Continue
Be the first to know
Get browser notifications for breaking news, live events, and exclusive reporting.