One of my favorite locations to visit. I love the vibrancy of a pedestrian friendly city. I love…read morethe people, the sights, the shopping. There is something for everyone

Attended the Choose Chicago Open House this year and very happy with my experiences. Able to check…read moreout 5 really cool establishment: Mindworks, Chicago Symphony, Federal Reserve, Wintrust Vault and Red Building (333 S. Wabash). All in all a very good experience. I wish that I would have gotten started earlier in the day. I liked the ventures on the app which allowed me to set up an itinerary. Some locations that I wanted to see were closed on Sunday. Favorites spots were the Federal Reserve and 333 S. Wabash. This event only happens once per year but really a good opportunity to check out over 120 buildings in various neighborhoods for free. Very neat experience and if you love history, architecture or sight seeing then this free event is for you.

This visitor center is a great place to start your visit to Chicago. They have docents that offer a…read morenumber of free tours of the area including a great two hour tour of Millennium Park. They are also knowledgeable about other excellent tours by the Chicago Architectural Foundation and other Chicago highlights. The Chicago Architectural Foundation is a few blocks south on Michigan Avenue and is also very worthwhile.

We visited Millennium Park during our weeklong stay in Chicago. We cut through the park a few days…read moreto get to the Art Institute and Symphony Center. However, we also spent a longer amount of time at Millennium Park for Chicago Blues Festival 2026. It's home of the Bean. I'd been telling my husband about Cloud Gate/the Bean for a while leading up to our trip. So it was a treat to point out the landmark to him on his first trip to Chicago. It's so nice that the city holds CBF there, what a great music fest experience with the Pavilion and all the other stages set up.

Cloud Gate aka The Bean & Millennium Park are some of my favorite things to do and see in Chicago…read more I try to swing by on each visit. There's just something so timeless and incredible about the sculpture by Anish Kapoor. The stainless steel structure is over 100 tons. It's a beauty and as you can imagine an extremely popular tourist attraction much like the park itself. Millennium Park is 25 acres and it includes other noteworthy sights: Crown Fountain-Created by Jaume Pensa. It's a water feature with two glass towers that projects faces of folks. Very cool thing to see. Lurie Garden-I love this space. It's close to 4 acres of flowers, shrubs, trees, and plants. An amazingly peaceful get away in the heart of a thriving metropolis. Pritzker Pavilion-This is one of my favorite Frank Gehry creations. It's magnificent. The design is impeccable. They have an incredible sound system so if you're there for a live music performance you're able to hear it from across the lawn. Great place to catch a movie in the park or a band. All-in-all it's a spectacular place to visit & wander whether a local or a tourist.

This is our 2nd Caravan Tour which started in Rapid City on June 6th & ended ten days later in Salt…read moreLake City. Mike DeAngelo a retired park ranger guided us through the Badlands, Yellowstone & the Grand Tetons. He had daily readings, good jokes, inspirational videos, and really made our trip special. Our group of 43 had varied interests & fitness levels & Mike managed to cater our activities to everybody . Ray drove a luxurious motor coach along rural roads. He got us through bad traffic jams, managed to park in some tough spots and always had a bottle of icy cold water on hand. When he wasn't driving the bus, he was cleaning the windows, emptying our garbage, and filling his basket of snacks. Like our previous tour, Caravan took care of our luggage, tickets for attractions & whisked us from place to place. Hotels, many meals & tours were arranged. Pointed out were things not to miss & they were missed the first couple of times we came through these parts unescorted.

Simply put, this was a terrible tour. Up every day too early and the days were too long. By the…read moretime we arrived at our hotels, nothing was open. Most were too far away from anything, We were told to "take an Uber or cab" if we wanted to explore. Lunch stops were too long, would've had more time to explore. By the time you got to the hotels you were too exhausted. The Hotel in Vermont was the worst. First they put us in a room with one bed, while they had plenty of 2 bed ones. Only one restaurant was open by the time we got there, it was good but way too expensive. All the shops were close but were closed by the time we got there. Place was run down and rooms had alot of damage. The "breakfast" was a joke, not even continental. Newport was one museum (with a rude staff) and a long lunch stop. Mystic was barely 2 hours. Both were in one day. The lunches were not included, that was stated and expected. However, we always stopped in small towns with not much choices. All were expensive and weren't grab and go. How about a fast food joint? Rest stop? 7-11, etc.? Our tour guide Lynn was not terrible. Talked way too much about her personal life. She talked way too much as well. She mentioned her final tip at least 4 times, very crass and rude. Never really led any of our the tours besides on the bus, mostly dropped us off and picked us up. She changed alot of the tour to her liking, we bypassed alot that would have been more interesting. Saying " this place is great, but we don't have time" or "you can come back to see it". That's why I'm here now. We also had to leave early the last day beacuse 2 people out of 48 had an early flight. Tour started all flights after 12pm, she inconvinced the entire bus for 2 guests. We were all dumpped off at 9am at terminal A at Logan, most had fights out of other terminals and were told we can walk, or catch a free shuttle, or "tour Boston one last time". Not stated in the tour description. I could've caught a much earlier flight home. There were also alot of older people on the tour, including my father. She refused to adjust the tour to their needs. Everything was a long walk with few choices. Long days with short rest. Positives (reason for the one ) Our driver Joel. Joel was witty, funny and very nice. He is an excellent driver and was and always on time. He knew more about the destinations than Lynn. We met very nice people from all over the country, in particular many fine southern men and women. They were the best part, friendly and funny, lots of fun and laughs were had. Boston, Martha's Vineyard, Cape Cod, Plymouth were the highlight. Portland was nice as well, but we should've stopped in Kennybunkport as well. The final hotel in Ogunquit was beautiful and tge town was a close walk, right on the ocean, wish we had more time there. Simply put, i will never use Caravan again. Our first tour our west they were awesome, accommodating and our tour guide Tom was great. We had a few hiccups, but they were dealt with. Very disappointed

We finally did it! Our family trip to Europe. Our boys are big history buffs like my husband and…read moreasked for a trip to Europe to visit specific sites/locations they chose. We decided to start planning and quickly realized we were over our heads. We found Windy City by searching online. Dana did an amazing job of listening to our wants/needs while guiding us to make wise choices as we went along. It was a terrific trip that we will never forget and we are on to planning our next two trips with her already.

Windy City Travel helped us arrange a trip to London. Paula was very helpful in putting together…read moreour travel plan. Her assistance made the trip run smoothly and left us to enjoy a great experience in London.