Long Weekend in Chicago, Illinois, USA – A 4-Day Chicago Itinerary
There is so much to do or see in Chicago, Illinois, USA that you could easily spend a week there. However, getting away for a whole week can sometimes be hard. If you’ve got a long weekend to spend traveling, check out this 4-day Chicago itinerary!
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Check Out the Chicago CityPASS
It’s worth noting that you can get a prepaid ticket booklet called the Chicago CityPASS which gives you access to several of Chicago’s main attractions for a cheaper price than if you paid for each of the tickets individually. Although I don’t recommend it for this Chicago itinerary (because you wouldn’t get your money’s worth), it’s something to keep in mind if you plan on deviating from my itinerary or have more than four days to spend there. If you are thinking about visiting a majority of the major attractions in Chicago, the Chicago CityPASS could save you a decent amount of money, plus it has some extra benefits for some of the attractions like being able to skip general admission lines.
You can find more information about the Chicago CityPASS on their website.
Chicago Itinerary: Day 1
Magnificent Mile and Around
Whether you’re flying or driving into Chicago, arrive early in the morning or later in the day, I highly recommend spending a day just wandering around downtown. Michigan Ave. also referred to as the “Magnificent Mile” is the major shopping district of downtown Chicago. It has all sorts of stores such as Uggs, Forever 21, Nike, H&M, Addidas, Marshalls, Zara, and more. The area surrounding the magnificent mile is filled with every restaurant under the sun, Italian restaurants, pizza shops, steakhouses, and any other type of restaurant you can think of.
My boyfriend and I particularly enjoyed Fado Irish Pub, simply for the atmosphere (and of course the drinks). My favorite part was actually listening to Aaron Wilhoft perform live on Friday nights. If he happens to not be there when you visit Chicago, you can see what you missed on his website.
Chicago Itinerary – Day 2
The Cloud Gate (aka The Bean) and Millennium Park
Every Chicago itinerary needs to include a stop at The Cloud Gate, nicknamed “The Bean” for its shape, in Millennium Park. I’ll admit that when my boyfriend first mentioned that he really wanted to go to The Bean, I didn’t understand what the hype was. However, it actually turned out to be pretty cool. It’s made of stainless steel, meaning you can not only see your own reflection in the bean, but also the reflection of the entire city behind it. It’s unique shape makes for some unique distortions and cool pictures.
While you’re in Millennium Park, consider stopping over at the Jay Pritzker Pavilion to see its cool architecture.
Chicago Cultural Center
The Chicago Cultural Center is an arts and culture center used to host many free public events. Even if there aren’t any events going on at the Cultural Center when you visit, I still highly recommend stopping by. It’s detailed architecture makes it a beautiful place to walk around. The main architectural features are probably its two large domes, one on the north side of the building and one on the south side.
360 Chicago at the John Hancock Center
The John Hancock Center is full of various activities and fun. However, the main attraction I recommend visiting is the observatory on the 94th floor called 360 Chicago. If you have the money and the time, If you didn’t get the Chicago CityPASS, I recommend getting the sun and stars pass, which allows you to visit the observatory twice within 48 hours. This way, you can appreciate the cityscape and the way the city lights up at night.
The main feature of 360 Chicago is The Tilt. Its a “ride” that tilts you 30 degrees out over the city. 30 degrees may not seem like much, but when you’re being leaned out of the city, it certainly feels like quite a bit. The great thing about it is that you can step back off the tilt at any time if you get scared or uncomfortable.
This is a Chicago CityPASS location
The Chicago River cuts right through the middle of downtown. The riverwalk was design to allowed the public access to the river and give visitors a unique view of the city. No matter the season, the riverwalk is a great place to visit. However, if you visit during the summer, you can maybe catch a concert or boat tour.
Chicago Itinerary – Day 3
Shedd aquarium was at one point in time the world’s largest indoor aquarium and the most visited aquarium in the United States. While it no longer holds those records, it is still one of the most visited cultural attractions in Chicago.
While I’m no fish fanatic (after a while, fish are just fish to me), Shedd aquarium always seemed to have something spectacular to catch my attention. The aquarium was separated into sections, each section featuring a different part of the world. The fish in each section were the fish that could be found in that part of the world.
The aquarium has several educational shows throughout the day as well, where you can learn about various animals such as dolphins, sea lions, penguins, and more while watching them do cool tricks.
My boyfriend and I easily spent three hours at the Shedd aquarium. However, if you plan on visiting the aquarium with little ones, I suggest planning on spending a majority of the day there.
This is a Chicago CityPASS location
In the evening, head over to Chicago’s other popular observatory, the Chicago Skydeck in Willis Tower (previously named the Sears Tower). While 360 Chicago is famous for their Tilt, Skydeck Chicago is known for The Ledge. It’s a glass box that sticks out from the side of the building, literally allowing you to step out onto the city.
Personally, I liked the views from 360 Chicago better, but I thought the Ledge was a cooler experience. I’d have a hard time recommending one observatory over the other, which is why both of them made it into my recommended itinerary. If you have to choose, you can check out this comparison between Skydeck Chicago and 360 Chicago.
This is a Chicago CityPASS location
Chicago Itinerary – Day 4
Probably the most iconic part of Navy Pier is the Centennial Wheel, a large ferris wheel. It’s open year round, weather permitting. Towards the end of the pier, you can also get a really good view of the city. It also holds several free events from time to time, so make sure to check the calendar before you go.
Crystal Gardens is actually a wedding venue, but part of it is open to the public to explore if there aren’t any events going on. The gardens is entirely inside, so even if you go to Chicago in the winter, you can enjoy the gardens. It’s most known for its “leapfrog” fountains, where water periodically “jumps” into several of the ponds.
Where to Stay in During a Long Weekend in Chicago
My boyfriend and I chose to stay at Best Western River North Hotel because we felt like it was a good middle of the road option. Since we were only going to be in Chicago for a few days, we knew that we likely wouldn’t be spending a whole lot of time in our hotel. We didn’t want to stay at a really fancy hotel that we wouldn’t be able to appreciate. However, because we were limited on time, we wanted to stay in or close to downtown for easy access to all our destinations.
Best Western River North isn’t located on the Magnificent Mile (the main street that runs through the middle of downtown), but it is just a block or two away. Plus, it’s surrounded by lots of fantastic restaurants and bars which make for great hang-out spots once you’re done sightseeing for the day.
Get more information about Best Western River North Hotel and book your stay at Booking.com!
And that’s it for Chicago! What do you think of this 4-day Chicago itinerary? Ever been to some of the places I recommended? Anything you think should be included in this itinerary? Let me know in the comments below!
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