If I could write a love letter to any U.S. city, I’d address it to Chicago. So many wonderful family vacations were spent here. I’ve been back multiple times and loved the city even more each trip.
There’s so much to do and see and eat that it practically necessitates multiple trips. But, for the sake of this 3 day Chicago itinerary, I’ll keep it down to one fantastic trip, and try to tone down how much I love it here.
Table of Contents
Official Language(s): none at federal level, English is considered the national language
Currency: U.S. Dollar
Emergency phone number: 911
When to Go to Chicago
March – April OR September – October
When I was little and my family first visited Chicago, my parents told me it was known as the Windy City. Walking along North Avenue beach, my little brain was all, “Yeah, makes sense. It’s super windy right now.”
Oh, my sweet summer child.
That’s actually not why it’s called the Windy City (it’s because politicians blow hot air), but still… it can get intense. Once, while walking from the Field Museum to Adler Planetarium, the wind was hitting me so hard I swear I got some mild weather-related version of whiplash. Adding to that, summer and winter are brutal. The shoulder seasons are your friend.
Sorry, I know I said I’d be concise. That’s not going well so far.
Plan to Stay
I’d recommend spending 3 days in Chicago. Make it a long weekend.
Where to Stay in Chicago
Hi Chicago Hostel
The U.S. still hasn’t jumped on the hostel train, so you’re a little limited in terms of options. HI Chicago Hostel has a great location, and is clean and comfortable.
24 East Congress Parkway, Chicago
How to Get Around in Chicago
CTA Unlimited Ride Pass
Certain areas of Chi town are easily walkable. To get to sights like the Museum of Science and Industry, all you gotta do is take the train. It can get a little delayed during Cubs games though, so do plan accordingly.
Where to Eat in Chicago
Ok so, let’s get this out of the way… you’ll need to try deep dish pizza. Obvious suggestion is obvious, I know. But I can’t have a guide for Chicago without mentioning it, so this is a quick little shoutout. Myself and the fam bam are all huge fans of Giordano’s. But realistically, there are so many great places to choose from for your pizza fix.
Side note: deep dish takes about 45 minutes to bake, so budget that into your schedule.
Alright, back to stuff that isn’t quite so in-your-face obnoxiously obvious.
The Gage is just a short walk away from the Art Institute, making it a perfect post-museum lunch stop. It’s a cute atmosphere; 20’s decor and a friendly staff that’ll recommend stuff to do on your trip. If you’re a fish person, this will be the place to order. My entree was so good, I wanted to lick the plate.
24 S Michigan Ave, Chicago
Rosebud on Rush
It’s hard to go wrong in Chicago’s food-based neighborhoods. My dad is convinced you could walk into any restaurant in ChinaTown and get the best dumplings of your life. Same logic goes for Little Italy. It’s all good. But the fam and I tend to sway towards Rosebud for their famous square pasta. And… the desserts. The desserts are huge. One slice of cake will feed a family of four. Ask me how I know this.
720 N Rush St, Chicago
Gibson’s Bar & Steakhouse
I think it’s kinda fun to eat at the original location where it all began. This is where it all began for Gibson’s, so it’s only fitting that if you want good steak/fish, you go here. You’ll want to make a reservation cause this place gets packed fast. And this will likely be your most expensive option. Which is why I’d recommend going there for lunch, it’s significantly cheaper then.
1028 N Rush St, Chicago
Kim and Carlo’s Hotdog Cart
Everyone and their mother recommended Portillo’s for the best Chicago-style hot dog. But if I’m honest, I liked Kim and Carlo’s Hotdog Cart much better. This may be sacrilege to some, so do you. For the uninitiated, “run it through the garden” is Chicagoan for “put everything you got except ketchup on it.” It’s my dad’s favorite thing in the world to say, so I always let him order.
499 E McFetridge Dr, Chicago
Day 1 of 3 Days in Chicago
It’s really called the Cloud Gate, but I’ve never met anyone who actually calls it that. It’s the Bean, ride or die. Go on and be touristy, take that photo of yourself at that weird angle. We all have.
Afterward, go ahead and wander through the area. It’s a beautiful space. Check and see who’s performing at the Pritzker Pavilion (I saw Yo Yo Ma there one time). Walk through Maggie Daley Park and see what events are taking place. And take in the beauty of Lurie Garden.
201 E Randolph St, Chicago
For the soon-to be recommended activities, you’ll want the Chicago CityPass. It’s one of the few passes that I wholeheartedly endorse as not being a gigantic waste of your time and money. It’s actually feasible to see everything within their time frame. What a wild concept.
Here’s what you’ll use, and what you’ll pay for (assuming you’re interested in just about everything included);
- Shedd Aquarium: Included, plus extras
- Skydeck Chicago: Included for day or night admission.
- Field Museum: Included, plus extras
- Adler Planetarium Premium Pass OR Art Institute of Chicago – Fast Pass: Pick the Art Institute. Adler Planetarium pass is $12, about half of what it costs to get into the Art Institute.
- Museum of Science and Industry – Entry + 1 Ticketed Experience OR 360 Chicago Observation Deck – Express Entry: I feel like 360 Chicago and Skydeck are advertising more or less the same thing. Go with the Museum of Science and Industry.
Alright, back to the fun stuff.
Art Institute of Chicago
My dad calls this place the Artitute. Does everyone do that, or is this strictly a Dad Thing? Lemme know.
Anyways, this museum has to be one of the best collections in the midwest, possibly the U.S. as a whole. There’s so many amazing works of art. I never get tired of walking into the Seated Buddha, American Gothic or Nighthawks. I’m only just scratching the surface. No matter what sort of art you’re into, you’ll find it here.
This can get pretty overwhelming, so I recommend downloading their app and starting with The Essentials tour. It’ll take about an hour and give you an idea of what else might pique your interest.
111 S Michigan Ave, Chicago
Open daily 10 a.m. – 5 p.m. Open until 8 p.m. Thursdays
Everyone goes here for Sue, the giant T Rex skeleton. It’s way cool in person. But beyond that, I absolutely love the displays on ancient culture and artifacts. I could spend a lifetime in the Inside Ancient Egypt exhibit. The Northwest Coast & Arctic Peoples exhibit is such a treat to explore.
One of the perks of having the Chicago PASS is the added 3D movie option. I’m not saying you should pick Secrets of the Mummies but you should totally pick Secrets of the Mummies. Then we can freak out about what a badass Rameses II was in the comments.
1400 S Lake Shore Dr, Chicago
Open daily 9 a.m. – 5 p.m.
I have spent countless happy hours in Shedd Aquarium. It has a great view of Lake Michigan and an even better view of penguins, dolphins and beluga whales. If you time your visit right, you might even be able to catch a whale feeding, which is always way cool.
1200 S Lake Shore Dr, Chicago
Open 9 a.m. – 5 p.m. Wednesday – Friday, Open until 6 p.m. weekends, 7 p.m. Monday and Tuesday
The Adler is super high-tech and informative. Even if you’re not a planetary nerd, it’s still so cool to see it all unfold the way they have it all set up. Totally worth the $12 admission price.
1300 S Lake Shore Dr, Chicago
Open daily 9 a.m. – 6 p.m.
Day 2 of 3 Days in Chicago
Museum of Science and Industry
Happy sigh. Oh, how I love this museum. Get here when it opens and prepare to stay till lunch (or longer). Everything here is so hands-on and interactive, and there are exhibits for everything. Wanna see a baby chick emerge from its egg? Covered. Wanna tour an old war-time submarine? Done. Curious how toys are made? They gotcha.
Again, a Chicago PASS will get you a bonus ticketed experience. Do the Coal Miner Tour. IT’S SO COOL OHMYGOD!
5700 S Lake Shore Dr, Chicago
Open daily 9:30 a.m. – 4 p.m.
The Magnificent Mile is way fun to wander around without an itinerary and just see what you spot. It’s home to luxury shops, the Historic Water Tower, Fourth Presbyterian Church and much more.
Chicago History Museum
I never see this place as crowded as other spots I’ve mentioned, which is a shame because this museum is a gem. You’ll want to start on the second floor, and work your way through from there. It’s an incredibly detailed look at the city’s history, and it’s masterfully done. You’ll emerge feeling much more connected to Chicago.
1601 N Clark St, Chicago
Open 9 a.m. – 4:30 a.m. Monday – Saturday, 9 p.m. Tuesday and 12 a.m. – 5 p.m. Sunday
Think of just about any famous comedian. A late night host. An SNL alum. A standup legend. There’s an excellent chance they got their start in Second City. It’s where the funniest people go to make it big. Doesn’t matter which show you end up choosing, you’ll laugh till you cry.
1616 N Wells St, Chicago
Day 3 of 3 Days in Chicago
Walk along North Avenue Beach
Your final day here is going to be all about the water. Start off with a stroll on North Avenue beach. If the weather cooperates and the lifeguards are on duty, bring a swimsuit and take a dip. Or rent a kayak. Or a bicycle. Or play chess on one of the painted squares located throughout the park.
Or… just chill, and take in the view. I think Chicago looks prettiest from here, don’t you?
Architecture Boat Tour
Cliche? Maybe. But an architecture boat tour is an amazing way to see the city. The tour departs multiple times throughout the day, giving you the option of a mid-afternoon or evening cruise. Up to you.
One Last Thing
The wait to get in line for Chicago 360° or Skydeck Chicago is almost always several hours long. Honestly? Your time is better spent exploring the city.
Pin me so you’re ready to explore the city with this 3-day Chicago itinerary!