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Chicago Dine-Around

Certificate of Excellence
Downtown / The Loop
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Address: 70 W. Madison St., Chicago, IL 60602
Phone Number: 312-437-3463
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9:00 am - 9:00 pm
Closed now
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Sun - Sat 9:00 am - 9:00 pm

Embark on an adventure to Chicago's best restaurants aboard Chicago's...

Embark on an adventure to Chicago's best restaurants aboard Chicago's premier Progressive Dining Tour. Guests are chauffeured around Chicago in a stylish coach bus to enjoy Hors D'oeuvres served at the first restaurant, the Main Course at a second restaurant, and Dessert at a third restaurant. The tour offers a unique, fun and exciting way to experience different restaurants in Chicago, interact with others, and tour Chicago. Visit our website for details and sample menu.

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TripAdvisor Reviewer Highlights

Read all 326 reviews
Visitor rating
  • 264
  • 44
    Very good
  • 5
  • 7
  • 6
Retirement Outing

Wonderful outing! Great food and a lot of fun! Our guide was very organized and had a great personality for this group of ladies! Would definitely like to do again!!

5 of 5 starsReviewed 1 week ago
Karen S
Naperville, Illinois

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326 Reviews from our TripAdvisor Community

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Date | Rating
  • English first
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English first
Naperville, Illinois
1 review
5 of 5 stars Reviewed 1 week ago NEW

Wonderful outing! Great food and a lot of fun! Our guide was very organized and had a great personality for this group of ladies! Would definitely like to do again!!

Thank Karen S
Bolingbrook, Illinois
1 review
4 of 5 stars Reviewed 1 week ago

Fun, fun and fun and more fun from the time we stepped on the bus until we stepped off. Our guide was great with just enough trivia to the mix. We were with a group of ladies that were fun and who did not know each at the start but walked away laughing and hugging.

Thank Cynthia S
Level Contributor
40 reviews
15 attraction reviews
common_n_attraction_reviews_1bd8 38 helpful votes
5 of 5 stars Reviewed 3 weeks ago

I arranged to have Chicago Dine Around pick us up in the suburbs (Glen Ellyn) and take us on a progressive dinner downtown to surprise a friend for his birthday. The driver arrived early at the exact spot we designated and we had plenty of time to do a few decorations to the bus. Each restaurant was ready and waiting... More 

Thank niu72
Toms River
1 review
5 of 5 stars Reviewed October 21, 2015

During Wyndham Hotel Group's Midwest Sales Mission, we incorporated the Chicago Dine-Around into our agenda as a very special client event. Brandon, our guide, was very knowledgeable of the city and definitely accommodating to our special requests including a few individual needing gluten free options. The three restaurants was visited (Troquet River North, Osteria Via Stato and Nacional 27) was... More 

Thank Dana R
2 reviews
5 of 5 stars Reviewed September 30, 2015

It was the most fun I've had in a long time. Bonnie our tour guide was so much fun and had trivia about Chicago !! The food and service was excellent . The driver Sonny was always there to pick us up and take us to our next stop. I would suggest that everyone try this ! I've lived in... More 

Thank Kathy C
1 review
5 of 5 stars Reviewed September 28, 2015

Had a wonderful time. Great night out with friends.Bonnie our guide was a lot of fun. Restaurants were fantastic. Would highly recommend😊

Thank Jo-Ann R
Level Contributor
16 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 17 helpful votes
5 of 5 stars Reviewed September 20, 2015

Got picked up and taken to 3 different restaurants, one for wine and appetizers, then to dinner, then to Navy Pier for dessert. Had a great time. Brandon was a lot of fun and kept us entertained between stops. Fun way to spend the evening.

Thank Judgepam
Hamilton, Ohio
Level Contributor
24 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 22 helpful votes
5 of 5 stars Reviewed September 19, 2015

Our group of 21 women chose Chicago Dine Around's Progressive Dinner Tour & it was one great evening! Brandon was not only the guy I spoke with in coordinating the event, but also our tour guide on the bus & he was phenomenal! He took care of all the details & made sure we all had a great time. And... More 

Thank penguin2634
Chicago, Illinois
1 review
5 of 5 stars Reviewed August 17, 2015

The Dine around team was fantastic! They made sure to go above and beyond and accomodate all of the limitations for this event. They were super courteous, took care of all of the details and stayed in constant contact with me to make sure that the event went off without a hitch. They made the event planning process enjoyable and... More 

Thank Dots0426
Elm Grove, Wisconsin
1 review
5 of 5 stars Reviewed June 16, 2015

What an amazing night we had with Chicago Dine-Around. Brandon was incredibly accommodating and helped make the evening's bachelorette party a success. The food was delicious, the service was quick and the bus ride was entertaining. I would highly recommend this tour to bachelorette's and girls looking for a fun night out. Thank you again!

Thank MeganS1022

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Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Chicago Dine-Around and other visitors
2 questions
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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?

Staying in Downtown / The Loop

Neighborhood Profile
Downtown / The Loop
Often visitors' first stop in Chicago, The Loop is a good starting point to sample the city's energy and flavor. This central business district boasts Michelin-rated restaurants, upscale hotels, premier shopping, and enough arresting architecture to keep your camera busy for hours. You won’t find too many photo galleries of downtown Chicago without a shot of Millennium Park and Cloud Gate (“The Bean”), one of the most iconic landmarks in the city. A stunning skyline coupled with cultural attractions like the Art Institute of Chicago present a Downtown where work and play peacefully coexist.