Possible May intinerary

Question

Hello. I am hoping to get some tips here about our possible itinerary for our trip to Chicago, arriving May 5 to Midway at 4:30 pm and leaving morning of May 13. We are an active couple in our early 60s. Want to take walk around Millenium Park after arrival to stretch our legs. My husband has work meetings the 6th and 7th - evening of the 6th we are attending a baseball game at Wrigley Field with his coworkers, the evening of the 7th going to see the show Hadestown. We are staying at Homewood Suites Chicago Magnificent Mile. We love walking around outside so will want to stroll around the downtown parks, perhaps get to sites via walking and Divvy bikes as much as possible. I have not fully figured out what I will do with myself his work days yet but do know what we are interested the other days. I do know I have to take weather into account and not fully sure how far in advance I need to make reservations for things. Thinking of an itinerary something like this (have not researched restaurants yet) but open to suggestions as far as what days to do what, how much to squeeze in, etc.

Thur, May 8: 1 Do Mike's Bike Hike food tour, 4.5 hrs, includes Lakeshore ride. Later do the Riverwalk and if possible see Art on the Mart. Think we would want something light maybe to eat because a lot of food on the tour.

Friday, 5-9: Museum of Science and Industry, think most of the day for us here. Interested in Robie House also but not sure can be done by start of their last tour at 2:30 so may not. Would like to see Hyde Park area incl the university campus, 57th St Books?

Sat, 5-10: The Architectural boat tour, the Original Chicago Architecture Interiors Tour, then Willis Tower. Thinking of getting tickets to a Second City show.

Sun, 5-11: the Art Institute probably for a couple hours, check out Magnificent Mile but not big shoppers. This is my husband's birthday in addition to Mother's Day so thinking I should try to come up with somewhere nice to eat but have not tackled this. We like good food but are not foodies, per say - does not need to be fancy.

Mon, 5-12: Go early to the Shedd Aquarium - not sure how long this one will take - will see one movie there since included on City Pass, and heard to see the Beluga/dolphin show? Lincoln Park Zoo - I know they are not near each other but did not know when to plug the zoo into our itinerary.

**The things I have not included but we are interested in are the Buckingham Fountain - figured we would walk around and get here at some point, maybe day of arrival?; the 360 Chicago observation deck, and Navy Pier (think we may try taking the water taxi from here to the Shedd). If things I have missed that would be easy to see, open to those suggestions also.

Thank you so much for any help you have with my itinerary! Excited to be coming to Chicago.

Answer

Your itinerary for Chicago looks fantastic, and it sounds like you have a great balance of activities. Here's a breakdown with some additional suggestions, tips for timing, and thoughts on when to make reservations:

For the first day, you’re arriving on May 5 at 4:30 pm and planning to stretch your legs at Millennium Park. This is a great idea, as it’s right by your hotel. Afterward, consider a relaxed dinner somewhere nearby, like at The Walnut Room or The Purple Pig, which both offer great dining options within walking distance of the park.

Thursday, May 8: Mike's Bike Hike food tour with a Lakeshore ride sounds like a fun way to start the day! If you’re planning to see Art on the Mart (the digital projections on the Merchandise Mart building), you’ll have a perfect view from the Riverwalk after the tour. It's easy to spend the rest of the evening strolling around the Riverwalk and enjoying the architecture. For dinner, consider a casual option, like Fried Chicken at Parson’s Chicken & Fish for a light but tasty meal.

Friday, May 9: The Museum of Science and Industry can easily take a full day, especially with the many exhibits and interactive displays. Robie House is also nearby and worth a visit if you can fit it in before the last tour at 2:30 pm. Hyde Park is a charming area to explore, and 57th St Books is a lovely independent bookstore. If you're interested in visiting a local coffee shop, Valois Restaurant is a popular spot for breakfast and a true neighborhood institution.

Saturday, May 10: The Architecture Boat Tour is a must-do and can take around 1.5 hours. Afterward, the Original Chicago Architecture Interiors Tour is an excellent way to dive deeper into Chicago's famous architecture. A visit to Willis Tower is a great way to get a panoramic view of the city—though consider timing it well with your other activities. If you're planning to go to a Second City show, make sure to book tickets in advance as those shows can sell out, especially on weekends.

Sunday, May 11: The Art Institute is a great way to start your day. Spend a couple of hours there to see the highlights. For your husband's birthday and Mother’s Day dinner, consider a great Chicago classic like Shaw’s Crab House for seafood, or Bandera for a lively but not overly fancy spot with delicious American fare. Both are excellent options for a celebratory meal.

Monday, May 12: Visiting Shedd Aquarium in the morning is a good idea, and you can spend a couple of hours there. The Beluga and dolphin shows are enjoyable, and it’s also nice to explore the other exhibits. The Lincoln Park Zoo is a little further north but can be a nice walk or short cab ride away if you’re interested in seeing the animals. If you're using your City Pass, consider taking the water taxi from Navy Pier to the Shedd—it’s a scenic way to travel, and you’ll get beautiful views of the lakefront.

Additional Suggestions:

360 Chicago (John Hancock Observatory) is another excellent spot for panoramic views of the city, and it’s close to your hotel.
Buckingham Fountain is a great quick stop if you’re near Grant Park and is best seen in the late afternoon or evening when it’s lit up.
Consider adding The Chicago Cultural Center to your list if you're interested in free art exhibits, music, and architecture. It's located near Millennium Park.
Navy Pier has a lot of fun attractions, but I’d suggest visiting in the morning or early afternoon to avoid the crowds. The Ferris wheel offers great views of the skyline and lakefront.

As for reservations, it's a good idea to book some of your activities and restaurants ahead of time—especially for popular attractions like the Architecture Boat Tour, Second City, and the birthday dinner. Chicago can be busy in May, so booking in advance for tickets and dining can ensure you get the spots you want. Since your trip is in early May, the weather should be mild, but always keep an eye on forecasts to make sure your outdoor plans can go smoothly.

Your itinerary looks well-balanced, with plenty of outdoor walking, cultural stops, and a nice variety of activities. Enjoy your trip, and happy travels to Chicago!

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