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Chicago Dine-Around

Certificate of Excellence
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Address: 70 W. Madison St., Chicago, IL 60602
Phone Number: +1 312-437-3463
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10:00 am - 10:00 pm
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Sun - Sat 10:00 am - 10:00 pm

Chicago Dine-Around specializes in unique and interactive dining...

Chicago Dine-Around specializes in unique and interactive dining experiences for corporate and private events. We offer Progressive Dining Tours, where guests travel in a stylish coach bus to the first restaurant for hors d'oeuvres, the second restaurant for the main course, and the third restaurant for dessert. Enjoy Chicago's renowned cuisine while you interact with different colleagues at each restaurant and learn about Chicago along the way.

Chicago Dine-Around also offers Interactive Culinary Experiences, Dinner and a Show, and Architectural Dining Cruises. Our events are ideal for meetings, networking, team-building, client appreciation, holiday parties and all types of corporate and private events.

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TripAdvisor Reviewer Highlights

Read all 329 reviews
Visitor rating
  • 267
  • 44
    Very good
  • 5
  • 7
  • 6
Brandon goes the second mile to make certain that everything is perfect from start to finish

Dine-Around Chicago provides a unique and fun opportunity to enjoy Chicago Dining and Culture along with sighting-seeing. The attention to detail is amazing and hands-on with a... read more

5 of 5 starsReviewed 1 week ago
Mary F
Brunswick, Georgia

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329 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Brunswick, Georgia
Level Contributor
10 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 1 week ago

Dine-Around Chicago provides a unique and fun opportunity to enjoy Chicago Dining and Culture along with sighting-seeing. The attention to detail is amazing and hands-on with a smile to ensure your enjoyment and pleasure with everything offered. Whether you are a resident or visitor, your contact with Dine-Around will be awesome and unforgettable. The food is absolutely delicious and offers... More 

Thank Mary F
Chicago, Illinois
1 review
5 of 5 stars Reviewed 1 week ago

We booked Chicago Dine-Around as a workplace team outing, and really enjoyed our experience! It was so fun to try out multiple restaurants and have the opportunity to socialize with different people in the group at each location. Brandon was a great guide, I definitely recommend this for any group outings!

Thank stefaniw w
Downers Grove, Illinois
1 review
5 of 5 stars Reviewed 2 weeks ago

Two weeks prior to an executive meeting, I was given the responsibility of finding evening entertainment for everyone. After doing some research online, I decided to give Brandon at Chicago Dine-Around a call to see if he could accommodate us on a Wednesday evening. Fortunately, there was availability for the progressive dinner. I opted to upgrade to the mid-range level... More 

Thank Angela E
Naperville, Illinois
1 review
5 of 5 stars Reviewed November 19, 2015

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 November 18, 2015

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
39 reviews
16 attraction reviews
common_n_attraction_reviews_1bd8 33 helpful votes
5 of 5 stars Reviewed October 30, 2015

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 via mobile

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 via mobile

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
19 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

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Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Chicago Dine-Around and other visitors
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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.