Arriving on Saturday morning in a few weeks leaving the next day, Sunday in the afternoon. What is the best way to utilize the limited time? Hotel recommendations?
Give us some hints what you like. Museums? Shopping? High end eating? Iconic inexpensive restaurants?
Any unusual museums? I know of the art institute of chicago. No shopping unless there’s unusual shopping experience unique to Chicago. Eating will be great both high end and iconic restaurants.
I would definitely do the architectural and lake boat tour. Fascinating fun tidbits and a wonderful way to spend 90 minutes.
Definitely go to top of John Hancock building for the bar. If you’re a female you must go to the ladies room!! Awesome views. Top of Sears tower, Millennium park and get picture of the Bean. Do Chicago River architecture tour. Eat at Lou Malnati’s a famous deep dish pizza eatery. Also Lou Mitchell’s for breakfast, Portillo’s for meat sandwich and Chicago hot dog and Ed Debevich for diner type food and atmosphere
The Navy Pier is nice and must get Chicago mix popcorn at Garretts while there
@CALSmom Great list!
There are a bunch of boat tours, but you should try to get a reservation on the one sponsored by the Chicago Architecture Foundation. It’s wonderful, and a completely reliable, fun, educational, unique thing to do there.
Also, plan to visit the Millennium Park area of Grant Park along the lakefront in the Loop. That’s where two famous sculptures are: Cloud Gate (a/k/a the Bean) and Crown Fountain. They are both super-crowd-pleasing monumental public art, fun to look at, and even more fun to look at people looking at them. In a short stroll from there, you can see some lovely public gardens, Frank Gehry’s Pritzker Pavillion, and the innovative Mary Daly playground. You could spend hours there, or 20-30 minutes, and feel happy either way.
I believe Ed Deblevic’s closed. Sad day.
Portillo’s - I recommend the chopped salad (amazing!), a Chicago dog and if you have room, the chocolate cake. 
Garrett’s - one to eat while walking, one bag to take home.
For a out of the ordinary museum my S enjoyed this museum when he was student teaching a couple years ago in the Pilsen neighborhood: http://nationalmuseumofmexicanart.org/
My pizza recommendation would be Pequods. Lincoln Park area.
I don’t know your taste in hotels, but we like staying at the Palmer House Hilton. Convenient location at a reasonable price in an interesting building. Get a room away from the elevators.
Another vote for the Chicago Architecture Foundation boat tour.
Last time I was there visiting my D, we really enjoyed a free Lyric Opera preview concert at Millenium Park. We also really like the Art Institute.
I suspect there will be fireworks at Navy Pier on a Saturday night in summer.
Any time I’ve been to the Shedd aquarium it’s been unbelievably crowded. We love aquariums but are not fans of the Shedd.
Love the art museum. Loved the boat tour. Been to the museum of science and industry http://www.msichicago.org and really liked it.
Lots of great hotels, any chain you can think of. I would find a great price in the Michigan Avenue area and go from there. I’ve stayed at the doubletree, nice. A kimpton in the theater district, nice but a subway ride from the main shopping areas. I’ve read trip advisor reviews and went with a national chain in a great area and never have been disappointed. I’m not super picky though.
Also I’ve been to the Navy Pier but it wasn’t my favorite. For one day, I think it’s a miss.
Definitely the bathroom at the top of the Hancock building! Stay and have an expensive drink and enjoy the views.
I would say you can stay at any hotel where the price is right (taking Tripadvisor feedback into consideration). With Uber & Lyft, getting around is easy, even if you aren’t right near an el station. I recommend the art museum, the Field Museum, the architecture tours. I would not waste my time waiting in lines at restaurants in the loop area (thinking about places like The Cheesecake Factory). Yelp restaurants … lots of great Yelp feedback in Chicago. If you like coal-fired pizza, I love La Crosta Woodfire Pizzeria Italiana.
All good suggestions! Here’s a few more
The Chicago Riverwalk is open - www.chicagoriverwalk.us for ideas - live music, places to eat/drink outside, could rent kayaks, boat tours, etc. I like City Winery
Agree w/ Chicago Architecture Boat tour- relaxing, nice way to see the city and interesting.
Millennium Park- google the monthly schedule and you will see they have lots of live music offerings on Saturday evenings. As someone noted upthread there are fireworks around the Navy Pier area but can be seen anywhere on the lakefront. I believe they go off about 9:30.
Palmer House Hilton as already mentioned is a nice location to stay- its near MP The Gage Restaurant across from the park is good.
Restaurants – I like the newer up and coming West Loop area – Girl & the Goat, Grace, The Publican, Green Street Smoked Meats, The Parlor, Avec, Au Cheval ( burgers - very different but often a line ),
Peaquods for pizza as mentioned- more than 1 location
Lincoln Park Zoo and lagoon - a nice place to walk around
There are lots of festivals on Chicago summer weekends - Blues fest, Taste of Chicago, etc, etc…It’s a lively city- a stroll along the lake early morning is always beautiful, imo
Enjoy!
Lots of rooftop bars – go have a drink up high - not a fan of the Hancock- try Cindy’s Rooftop or google rooftop bars and you will there are plenty
Another vote for Pequod’s Pizza – the crust is amazing.
And if you have a few extra thousand dollars to burn, you could always try to get tickets t “Hamilton.”
@Iglooo thanks! I’ve done Chicago in day once and another trip Chicago in two days. I love that city!! If you’re a shopper, I visited Marshall Fields back in 2007 (took the famous L train) and ate at The Walnut Room (fantastic).
Last time I was there in 2013 I stayed at Marriott Residence Inn I think. I loved the location and was walking distance to a great piano bar.
There’s a Frank Lloyd Wright tour that we attended and enjoyed a two years ago. It was informative and we saw several of the homes he designed in a small, walkable self-guided tour. We also enjoyed the architectural boat tour.
Only one day??? Too much to do.
Definitely stay in a Michigan Ave area hotel- use online sites for the one you want. Weekend prices on all those business serving hotels are a lot cheaper than weekdays. Be sure of location- you do not want other nearby areas with such limited time.
A boat trip or bus tour are both excellent ideas. I agree with not spending your few hours with Navy Pier, although they have a great free stained glass museum. Too many museums for you to choose from as well. If you can get hold of the AAA tour book look at their listings and maps.
Excellent architecture, great seen from the water. Find time to walk along Michigan Ave and the lakefront parks. You will leave wishing you had more time. We used to make weekend trips from Wisconsin frequently until we retired to FL. Can’t beat the museums et al.
We just did this! In the morning we did a food tour with Chicago Food Planet. Then walked back towards the river via the magnificent mile. Took a boat tour and then headed for a drink at the Trump roof top bar. We walked back to our hotel JW MArriott and stopped by The Millennium park to see the bean. We had a great day! Exhausting but so much fun.
D & I just got back from our 60/30 Hamilton weekend in Chicago 10 days ago. We stayed at the Fairfield on Ontario because it was the only Marriott property where I could use points for the weekend. It was very nice and, of course, Fairfield’s have free breakfast. Easy walking distance from so many things. I have been many times, but we did a few things I had never experienced. One was the Driehaus Museum on Erie on Friday and that was an interesting example of period architecture. On Saturday morning we did the boat architecture tour and I loved it. I knew I would love Hamilton, but loved the river tour almost as much. After that we had lunch nearby and then walked down to the Art Institute which we have visited many, many times. Whistler’s Mother was there, but that exhibition ended on 6/11. One of my favorite art museums of the many my family has visited through the years. If you have a Bank of America credit card, you can get in free (D did, but I had to pay).
You could do all 3 of these in one day, but it would probably be more relaxing to pick 2.
@Iglooo I remember now. I stayed at Marriott Residence Inn on N. Dearborn Street (Chicago Downtown /River North location). Walking distance to plenty of good restaurants and that super fun piano bar! It included breakfast which was great and the staff was friendly and attentive. I took Lyft everywhere from my hotel