Speed Date a City - Chicago!

Chicago, IL, USA

4 reviews
Sep 29 - Oct 2, 2022
Group size: 4 - 8
Speed Date a City - Chicago!
Chicago, IL, USA

4 reviews

Sep 29 - Oct 2, 2022
Group size: 4 - 8

About this trip

Another chance to Speed Date a City - this time it's the 'Windy City' of Chicago.  Interestingly, the term was coined in 1893 and referred, not to the weather conditions, but to the verbosity of the politicians!

We will be centrally located in the Loop, close to all the action.  We'll have drinks on top of the John Hancock Building to see all the lights, go for an architecture walking tour where we see both the outside - and inside - of the beautiful buildings, visit the renown Art Institute, wander around Millennium Park (and take selfies by the famous Bean), and see the city from the River on an evening boat tour.

There will be no more than 8 ladies along - and everyone gets their own room at no extra charge!  NOTE:  Although there will be no strenuous hiking, we *will* have a 90 minute walking tour and will be doing some walking around the city.  Please discuss any mobility issues with me ahead of time so we can be sure you will enjoy the tour fully.


What’s included

  • Accommodation
    Your own single room at no extra charge!
  • Ground Transportation
    Wherever we need to go in the city
  • Admission
    Art Institute Museum
  • Walking tour
    Dazzling Interiors of the Loop
  • Boat tour
    Chicago Sunset Cruise
  • Airfare
  • Airport transfer
    Transportation from airport to hotel



We will meet at the hotel in the afternoon.  Although airport transfer isn't included, Chicago's public transportation is excellent and there are, of course, cabs & Ubers available too.

Once we've checked into the hotel, we will head out for cocktails at the Signature Room atop the John Hancock Center where we can enjoy the city lighting up beneath us.

Dinner will be nearby.

Your Organizer

Sheila Stone Tours
4 reviews
I’m Sheila Stone and I love travel so much that I started a tour company when I was 60. (Have I mentioned that I’m also a late bloomer?) I create and lead small groups of women to interesting places like London, Scotland, Ireland & Japan. I have some tours in The States too. In addition to the usual sightseeing, my tours give women an opportunity to meet local women. By staying in small hotels and eating at family restaurants as much as possible, our travel money stays in the communities we visit. A fun way to meet like-minded women!


Thank you Sheila for a fabulous time in Santa Fe. Everything was perfectly set up for us. The Hotel was in a great location. It was very clean and included breakfast. The museums were so interesting. Sheila is a delight to travel with. So organized. I definitely will travel with her in the future. I'm still thinking about the delicious chocolate tasting!
By Judy m for SPEED DATE A CITY: SANTA FE on 05 Apr, 2022
What a great weekend in Santa Fe. Sheila is a great organizer and everything ran smoothly. Action packed but with plenty of time to walk around and relax. We hit some great spots and I don't think we missed anything. Sheila did a great job and it was just a fantastic trip. Caroline
By caroline.marshall@cshs.org for SPEED DATE A CITY: SANTA FE on 28 Mar, 2022
Really fun four-day weekend! Sheila is a knowledgable tour guide, and was able to pivot when we needed to make changes to the itinerary, and she also kept our needs in mind. I had a great time and hope to join her on another one of her tours!
By Lynne L for GALentine's GETAWAY WEEKEND on 23 Feb, 2022
The Christmas Holiday Tea in Santa Monica was wonderful. Sheila always organizes great events. We all had fun getting to make new friends!
By janet c for Los Angeles Christmas Afternoon Tea on 13 Dec, 2021


The Wild About Harry Tour was amazing! My kids and I had a fantastic time. Sheila was great in making sure we saw as much of Harry Potter that London and Oxford have to offer, and she was also helpful in getting us to see the cities and planning our side trip to Paris. This is a once in a lifetime opportunity that we will never forget, and we talk about constantly. Thank you!
By Denise R on 21 Jul, 2021
Thoroughly enjoyed my Bayou trip with tour host Sheila and local host Andrina. Great mix of fun sights including Mardi Gras museum, local food, shopping, bars and music in NOLA. A powerful Whitney plantation visit. Andrina hosted a traditional crawfish boil and an amazing get together with women of the local area representing the various cultures of the region. Felt like visiting with friends and family. Highly recommend this trip! Sheila is a great guide and trip planner.
By Nancy F on 19 Jul, 2021

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