4 Day Chicago Itinerary (So You Don’t Miss Anything!)
I’m going to tell you EVERYTHING you should have on your 4 Day Chicago itinerary. (Because you won’t want to miss anything!)
I’ve always felt like this city is such a hidden gem. It’s not New York or LA, you don’t hear about it on the news like you do about what’s happening in Washington DC, and it’s not located on the east or west coast where it could be included on a popular costal USA roadtrip.
In some ways I feel like Chicago is an island in that there’s a lot going on inside of it, but not quite as much going on surrounding it. If you drive just a short distance outside of the city you’ll find fields, farms, and much smaller towns by comparison. This little (big) Midwestern gem has SO much to offer and it’s SO worth visiting. So when you do find yourself ready to take this trip (“when” not “if” š) these are all my recommendations on everything you should have on your 4 day Chicago itinerary. š
Go to a Cubs Game at Wrigley Field
First up on your 4 Day Chicago itinerary? A Cubs game at Wrigley Field of course! EVERYONE loves Wrigley. How could you not? Itās the second oldest ball park in America and itās where Babe Ruth famously called his shot before hitting a home run in the 1932 World Series. How cool is that?! No matter how well or not so well the Cubs are playing during the season watching a game at Wrigley is ALWAYS a fun time. If you’re visiting Chicago during the off season I still recommend seeing the stadium from the outside. The sign in front is famous! And if you’d like an inside look you could always take a tour of Wrigley Field.
Visit Chicagoās Museums
Thereās SO many museums in Chicago I couldnāt even begin to name them all off the top of my head. (Thankfully lists like this exist. š) My personal recommendations and the ones that seem most popular among Chicagoans and our visitors would be the Museum of Science and Industry, Shedd Aquarium, Field Museum, and the Planetarium.
Art Institute of Chicago
Yes this is another museum but I recommend it so highly on my 4 Day Chicago itinerary list that it gets its own little section. š In this museum youāll find various paintings by Monet, van Gogh, Toulouse-Lautrec, and so many more. Youāll also find the famous “American Gothic” painting and “Sunday in the Park” which you may remember seeing at this museum in the movie “Ferris Bueller’s Day Off.” This is a good one, guys. Check it out!
Navy Pier
Itās super touristy but you have to visit Navy Pier just to say you did. Itās where youāll find restaurants, souvenir shops, and a few fair type rides. If youāre visiting during summer Iād recommend swinging by on a Wednesday or Saturday night when there’s a firework show.
Sears Tower
Ok itās TECHNICALLY called Willis Tower but youāll never in your life hear any Chicagoan call it that. Itās Sears Tower. Period. š Iād say this is one of the most iconic buildings in the city and takes its place high up on the list of what not to miss in Chicago. Itās a little pricey but you can take an elevator to the top where youāll see some of the most incredible views of the city. This is also where youāll find those glass boxes if youād like to stand in one and look down below. šÆ
Hancock Tower
The Hancock Tower is another well known building in Chicago and it’s where you’ll find some more incredible views of the city. You have a few options on how to see these views…
The first is to visit the official Observation Deck. (This is where you’ll find the windows that tilt, if that rings a bell.) I recommend buying your tickets online in advance if you plan on going that route. The second option is to eat lunch or dinner at the Signaure Room which is the restaurant at the top of the tower. The menu is a little pricey as you can imagine, but the experience is pretty cool. And your third option is to visit the Signature Lounge which is the bar at the top of the tower. From here you can order a drink, appetizer, or dessert and enjoy the same views as you would at the Observation Deck or Signature Room for a fraction of the price.
And here’s my favorite little secret… The BEST view in the entire Hancock Tower is from the floor to ceiling windows in the women’s bathroom at the Signautre Lounge. TRUE STORY. (Sorry men, there’s no windows in your bathroom). You decide how you’d like to visit, but I may or may not have taken female visitors to the women’s bathroom to check out the view and then gone straight back down the elevator. Just saying… š
The Bean (Cloud Gate)
Another Chicago icon that doesn’t go by its official name… The Bean. It’s officially called Cloud Gate but you’ll never hear a Chicagoan call it that. It looks like a bean. So we call it the bean. š It can get super crowded here during the day, but if you visit around 7am you just might have it all to yourself.
Millennium Park
Right behind the Bean is beautiful Millennium Park. The best part about this park is the free concerts the city puts on here during the summer. Bring a picnic, find a spot on the grass and enjoy this local experience.
Lincoln Park
Lincoln Park is a neighborhood in Chicago, but it’s also the name of an actual PARK in Chicago. The views of the city from here are incredible.
Lincoln Park Zoo
If zoos are interesting to you, the Lincoln Park Zoo is free!
Buckingham Fountain
Check out this iconic fountain and stay to see the water, light and music display that happens at the top of every hour. Check out the website for exact times (and months) the fountain is operating.
Kayak the Chicago River
It’s not every day you have the opportunity to kayak down a river while surrounded by giant skyscrapers in a bustling city. So why not try out some urban kayaking while you’re in town?! Urban Kayaks rents kayaks with the option of taking a tour or exploring on your own. Whichever option you choose I recommend renting from their Riverwalk location as it’s the closest launch point to the coolest areas of the city to see from the water.
Architecture Boat Tour
My personal favorite and #1 recommendation to have on your 4 Day Chicago Itinerary is this architecture boat tour. Chicago is known for it’s incredible architecture and what better way to see and learn about it all than during a guided tour on a boat ride through the city?! I recommend the Lake & River Arcitecture Tour with Wendella as it covers all the buildings and views along the river as well as all the buildings and views from the lake. Super thorough. š
State Street
Take a stroll down State Street and see the heart of downtown Chicago. Be sure to pass by the Joffery Ballet studio at the corner of State St. and Randolph, and the Chicago Theatre at State St. and Lake St. as both are icons in this city.
Michigan Ave
Take a stroll down Michigan Ave and see the famous Magnificent Mile. This is where you’ll find high end shopping, fancy hotels, cool restaurants and one of the oldest buildings in the city. (The Chicago Water Tower.) This isn’t a street I personally spend a whole lot of time on, but I still say you have to see it when you visit Chicago just to say you did.
North Ave and Oak Sreet Beaches
Soak in the sun at my two favorite beaches (“beaches”) in Chicago. (I’m from Califronia where a proper beach involves the OCEAN, so I have a really hard time talking about Chicago’s “beaches” without using quotations. š) These two are my personal favorite because of how easily accessible they are to the city and the gorgeous views they have to offer.
Bike the Lakefront Trail
Right along Lake Mighican is an incredible 18 mile lakefront trail that Chicagoans LOVE to make use of, and I totally recommend going for a bike ride on it. Rent a Divvy bike (more on those later) and pedal your heart out. š If 18 miles is a little ambitious for you, I recommend riding from North Ave Beach to the Adler Planetarium which is about 8.5 miles round trip and has the prettiest views on the entire Lakefront Trail.
Where to find the Best Views of the Skyline:
Adler Planetarium
Michigan Ave Bridge
North Ave Beach
Bonuses:
Chicago Tribune Building
The coolest features of the Chicago Tribune Building are the little pieces of other places that are all over it. And by that I mean there’s LITERALLY little pieces of other places embedded into the exterior of this building… Hagia Sophia, Notre Dame, Pompeii, the list goes on. Take a walk around the perimeter and see what significant places around the world are included here.
Green Mill
Visit the Jazz club that Al Capone frequented and see the booth (with a clear view of both doors) that he and his men would sit at.
Second City
Catch a show at Second City, the improv comedy club and school where Tina Fey, Stephen Colbert, Steve Carell and numerous others performed before the world knew their names.
Route 66 Sign
Did you know there’s a sign that marks the start of Route 66? It’s in front of the Starbucks on the corner of Michigan Ave and Adams St.
Where to Eat
I’m not a foodie by any means, but these are some mouthwatering Chicago favorites and my go-tos to take visitors when they’re in town. š
Bongo Room
This is my all time favorite place to go for breakfast. The menu has foods like white chocolate and caramel pretzel pancakes, gingerbread pear and vanilla french toast, banana praline hotcakes, need I go on? š You can find yummy savory foods here as well if for some crazy reason you’re not a sweets person. š
Giordano’s
If anyone tells you any place other than Giordano’s has the best deep dish pizza in Chicago they’re wrong. š
Portillo’s
Go to Portillo’s for a Chicago style hot dog! Whatever you do DO NOT add ketchup to it or it’s not a true Chicago style hot dog. *Bonus* If you’re a sweets person, order a cake shake. It’s a shake with an entire slice of chocolate cake blended into it and it might just be one of the best things EVER.
Bars
I should preface this with the fact that I don’t drink. So my bar recommendations have absolutely nothing to do with the drink menu and everything to do with the ambiance and views they offer. š
Cindy’s
London House
Getting Around
* Chicago has a great public transportation system and you can easily get to all the places I mentioned above via bus and train.
* Incase you haven’t experienced this yet, Uber and Lyft have a carpooling option in Chicago (among other cities). That means you can choose the carpool option (it’s always the cheapest) and share your ride with another traveler headed in the same direction. It may seem a little strange at first, but after a few experiences with it it feels totally normal. š
* Chicago also has a great bike share program called Divvy. It’s $3 for a single ride or $15 for a full 24 hours. The best part about Divvy bikes is that there’s docking stations ALL over the city. Which means it’s easy to pick a bike up in one location and drop it off somewhere entirely different. So convienent!
And I think that sums up Chicago! Phew… I had a lot more to say than I thought I would. š Let me know if this list was helpful for you on your trip to the Windy City! I’d love to hear about it. Chicago is an amazing city and I hope you enjoy visiting as much as I love living here. š
Safe travels friends.
CE
