Living in Upper Michigan and Minnesota for my first 40 years, Chicago was the biggest city that was within driving distance, making it a great long-weekend destination. There is such a wide variety of things to do in Chicago, from museums, to sporting events, to water sports, and great shopping! This itinerary assumes it’s not winter…if it’s your first trip to Chicago, do yourself a favor and don’t go between December and March. I’ve done trips to Chicago with my kids when they were young, for girls’ trips with my friends, and for a couple’s getaway. This itinerary was based on a trip in August with kids, but all of the activities are fun for all ages, and I’ve added a couple of extra ideas for the adults too. Lace up your walking shoes and save room for some Chicago style deep dish pizza!
Here is a sample 3-day itinerary for Chicago, based on our family trip with kids in August:
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DAY 1: MUSEUM OF SCIENCE & INDUSTRY AND SHOPPING ON MICHIGAN AVENUE
As far as where to stay, there are a ton of good options in Chicago, depending on your preferences. Just be sure to stay in the Michigan Avenue / Magnificent Mile area so that you can walk almost everywhere. I don’t recommend renting a car. For this itinerary, I’d recommend something in the Streeterville area. I’ve stayed at the DoubleTree Magnificent Mile which is a great option with an outdoor pool, or you could stay at the Fairmont Millennium Park. Both are nice hotels with all of the amenities in a great location. My kids loved swimming in the hotel pool, surrounded by the sky scrapers!
Travel Tip: If you plan to follow this itinerary for the most part, I’d recommend getting a Chicago CityPass here. It includes admission to many of the attractions in this itinerary, saving you money and getting those reservations lined up in advance so that you can skip the lines!
Since this was my kids first trip to Chicago, we wanted to hit all of the main attractions that Chicago is known for. There are quite a few museums, and since my kids were 7 and 10 when we visited, we tried to spread the museums out a bit. So if you’re on a similar track, grab breakfast at the hotel and grab an Uber to take you to the the Museum of Science and Industry. Other than the airport, this is the furthest you’ll go from the hotel during your stay. There are some staples there like the U-505 Submarine Tour, but there are also rotating exhibits that are really neat. We also did this sheep brain and eyeball dissection that was interesting…my son looks a little unsure in the picture below! I recommend buying your tickets in advance so that there’s no extra waiting when you get there, and plan on staying for 4-5 hours and having lunch at their restaurant on-site.
After a pretty full day at the museum, Uber back to the hotel for a little rest before heading out in the evening. Once you’re well-rested, put on your comfortable shoes (really you should be wearing them the entire trip!) and head North on foot up Michigan Avenue. There’s beautiful architecture and great shopping all along the way. Be sure to make it up at least to Water Tower Place Mall and catch a glimpse of the iconic John Hancock building. You can take an elevator to the top of the building where there are 360 degree views of Chicago (for a fee of course), but an alternative that I prefer is the Willis Tower that we will go to on Day 2. Take your pick, but it’s not necessary to do both. There are lots of good restaurants to choose from along the way, and be sure to stop at Garrett Popcorn shop to pick up a bag of Chicago Style popcorn to snack on throughout your stay…my favorite is the Chicago Mix (caramel and cheese corn)!
DAY 2: MILLENNIUM PARK, WILLIS TOWER, AND NAVY PIER
For Day 2, after grabbing breakfast at the hotel, take the 25-minute walk heading South to Millennium Park. There are a ton of things to do and see here, from gardens, to fountains, to concerts, and of course you can’t miss the famous bean! Be sure to take some fun pictures here.
When you’ve seen everything you want to see and have worked up an appetite, walk over to Giordano’s Pizza nearby. Don’t wait until you’re starving though, because they don’t take reservations and there’s usually a wait! This is Chicago style deep dish, so don’t be alarmed…the sauce is on the top! There are three main deep-dish places that I am aware of…Geno’s (famous for their cornbread crust), Lou Malnati’s (known for their layer of Italian sausage), and Giordano’s (famous for the insane amount of cheese they use). So depending on what your preferences are, pick your favorite Chicago-style pizza chain and go there!
For the next stop, it’s about a 25 minute walk, but hopefully you’ve had a long lunch and are rested up! Walk down to Willis Tower (formerly Sears Tower), the tallest building in Chicago and third-tallest in the Western Hemisphere. Again, I’d recommend getting tickets in advance through their website so you can avoid any lines when you get there. The highlights of Willis Tower are The Skydeck and The Ledge, which is a glass extension found on the 103rd floor where you can walk out and see straight through to the ground! It’s not good for those with a fear of heights…
After making your way back to the hotel (you might want to Uber if you’re tired of walking) and taking another rest, Navy Pier is a Chicago staple that is worth walking out to see. It’s about a 20-minute walk from the DoubleTree, and has lots of options for dinner, as well as carnival-style games, rides, and snacks. In the summer (Memorial Day through Labor Day), there are fireworks on Wednesdays at 9PM and Saturdays at 10PM as well. It can be crowded, so be prepared, but the kids (young and old) will love it!
If Navy Pier is not your idea of fun (it’s not really mine!), another great option for the evening on Day 2 would be to take an architectural river tour like this one from Viator. It might be a little boring for younger kids, but is a great way to spend some time off your feet. Or yet another option would be to see a broadway show at the theater. There are several theaters in Chicago that feature broadway shows like Wicked and Hamilton.
DAY 3: FIELD MUSEUM, SHEDD AQUARIUM, AND SOLDIER FIELD
For your final day in Chicago, grab breakfast in the hotel or at a nearby cafe, and then Uber to the Field Museum (you can walk as well, but it’s about a 50-minute walk from the DoubleTree). The Field Museum is a Natural History Museum (and one of my all-time favorite museums), featuring Dinosaurs like Sue the T Rex, and an Egyptian exhibit that’s really cool. There are other rotating exhibits as well, and a restaurant where you can have lunch. Plan on buying tickets in advance (or using your CityPass) so you can skip the line and go right in.
If you’re up for it, after spending a few hours at the Field Museum, walk next door to the Shedd Aquarium. If this wasn’t included in our CityPass, we probably would’ve skipped it. We did walk through pretty quickly (my kids were kind of burnt out by this point) and there’s neat stuff to see like these jellyfish, but if you have to choose only one major activity on this day, do the Field Museum.
If you’re football fans like we are (even if not Bears fans), another great option for Day 3 is to take a tour of the historic Soldier Field. Built in 1924, it’s one of the most iconic football stadiums in the world. The basic tour lasts about an hour, and includes stops in one of the sky boxes, the visitor’s locker room, and on the field. Of course if you time it right, you could also work a Bears or Bulls game in to your agenda.
For your last meal in Chicago, maybe splurge for something nice to celebrate a wonderful vacation…check out this article for some great options in Chicago!