Things to do in Chicago
I had never thought about going on a vacation to Chicago and had no idea what I wanted to do for a full week there. I knew about the Bean, but really not much else. Doing my research I found a lot of great things to do around the city! This post will go through what I did and some additional options to do and see in Chicago.
(Everything in blue is a clickable link)
Millennium Park (and surrounding area)
Cost: Free Hours: 6:00am – 11:00pm
This is an obvious and a must see while in Chicago! Cloud Gate is open from 6am-11pm, and they do not let you in when it is closed (we tried haha). For the best photos of the bean and with the bean I recommend going during the week and as soon as it opens or close to closing (with a good night time camera). I woke up with the sunrise, grabbed breakfast and was able to get over to the bean right before 7am on a Tuesday. There were only five other people there, which was great because we took turns taking photos of each other and tried to stay on different sides of the bean for great views and shots of it. As we were leaving, a lot of people started to come out to see it. Even though I had to wake up way earlier than I wanted to, this was a great experience and I got really great photos! I would have hated it being packed on the weekend or mid day.
Cost: Free Hours: 6:00am – 11:00pm
This fountain is an interactive video art sculpture located in Millennium park. The video sculptures on each side show people’s faces and them blinking, after a little while they will spray water out of their mouth. This is something cool to see after looking at the bean. It is a nice place to relax under the trees and listen to the water, or take the kids to run through the water during the warmer months!
This is a band shell within Millennium Park with a nice lawn in front of it and a large metal crossing sculpture above. Nothing was going on when we were there, but during the summer months there are free concerts and events at this pavilion! Click on the link to see what events are happening while you’re there.
Cost: Free Hours: Weekdays 12pm-8pm, Weekends 10am-9pm
This was one of my favorite (lesser known by tourists) places in the city. Maggie Daley Park is a park that has a huge playground, rock climbing wall, ice rink (in the winter months), and tennis courts. There is also a mini golf course that features miniature staples of the city. This park has amazing views of the Chicago skyline which is why it was one of my favorites. We were there before everything opened up, but were still able to explore. We took pictures next to the cute mini golf holes, photos of the skyline, and went up into the playground (I may or may not have gone down a few slides). I’m not sure if we were allowed to be on the playground but it’s HUGE and honestly big enough for adults! There was only one other family out there with their kids playing on the slides, so we were not in their way. If you have kids, they will love the playground!
I did not get to try the rock climbing wall but it is very large and looks like a lot of fun! During the winter, their skate rink is very large and allows you to skate through the park and not just in a small circle. Skating is free if you bring your own skates, otherwise there is a rental fee for ice skates. I would love to go back and try the skate rink sometime!
Grant Park – Buckingham Fountain
Cost: Free Hours: 6:00am – 11:00pm
Grant Park houses the impressing Buckingham Fountain and some beautiful gardens! We walked here after visiting Millennium Park and Maggie Daley Park (it is about a mile walk from inside Maggie Daley to the fountain). We were there during the opening game of the football season, so all of Grant Park was closed off in preparation for a pre-game party for the Bears. Because of this, we were only able to see the fountain from a distance. I would recommend going to see the fountain because it is very large and beautiful. Next time I go, I will have to take some photos there.
Broadway Shows
Cost: Varies, but typically cheaper than NYC
Another one of my favorite parts of Chicago is their Broadway shows! They have great headlining shows for less than you would pay in New York and the quality is just as good! I found out that Hamilton was in Chicago and I found tickets for only $52!!!! Obviously I HAD to go! My husband was less than thrilled, but we made a date day out of it and saw Hamilton at the 2pm showing on a Wednesday. Our seats were “obstructed view” because we were in the last seats on the left side (so we couldn’t see the farthest part of stage right), but we were only 4 rows back! Also the background dancers are on the sides in a lot of parts of Hamilton and both sides do the same thing (so we didn’t miss anything), and we could see the main characters the whole time. The show was AMAZING!!! My husband actually enjoyed the show as well! I couldn’t believe I got each ticket for $52 when I would have spent well over $100 per seat much further back in New York, and even the touring Hamilton show that came to Arizona had their cheapest tickets at $75. Broadway in Chicago is a must if you like Broadway shows!
City Views
A popular touristy thing to do in Chicago is to visit the Willis Tower or the John Hancock Center for some amazing views of the city. We went to both. There are also some great rooftop restaurants/lounges that offer good city views.
Cost: $26 Adults, $18 Children for General Admission Hours: 10am-9pm
Skydeck at Willis Tower is located on the 103rd floor of the Willis Tower where you can see amazing views of the city and walk on the “Ledge” glass boxes that extend 4.3 feet from the skydeck and 1,353 feet in the air! I wanted to come here for the Ledge experience. We bought the General Admission tickets for $26 each, but they also have expedited entry tickets for $80 or day and night tickets for $45 each. We were there in the fall and waited only about 20-30 minutes to get to the top. During the summer months they do get busy and you can expect over an hour wait. There is no time limit for how long you are up there and you can walk around and enjoy the views and take plenty of photos. There is an additional line for the Ledge experience and there are two Ledge boxes. We waited in the shorter line and had to wait about 15 minutes. There is no extra cost for the Ledge but you only get 3 minutes on the ledge. The workers there will take photos of you during that time if you would like. This experience was amazing and I got some really great photos. I’m not afraid of heights but it is a little scary looking down when you first step onto the ledge! This was a great experience, and I would love to see it at sunset next time!
360 Chicago at the John Hancock Center
Cost: $22 Adults, $15 Children for General Admission Hours: 9am-11pm
360 Chicago is located on the 94th floor of the John Hancock Center where you can see amazing views of the city. They also have “Tilt” which you can stand at a window that moves and tilts down towards the city (this is an extra $8).
Because we had already been up to the Skydeck at Willis Tower, we did not go up to 360 Chicago, but we did go up to the Signature Lounge on the 96th floor of the Hancock Center. It is free to go up there but you do have to purchase something, drinks (alcoholic or non) or food. We had to wait about 10 minutes to get seated but did not get a window seat. We did still have great views of the city, but I would have loved a window seat. You can request a window seat, but be prepared to wait much longer, and there are no reservations in the lounge. My husband and I both ordered a drink, and it was ok. Mixed drinks average around $17.50 each or beers around $10.50 each. You can walk around a little bit to get some pictures, but there are not many spots unless you have a window seat. Pro Tip: The view from the women’s bathroom is amazing!
I’d say its worth it because you can get a drink or an appetizer and have great views, so the cost is worth it. The service isn’t that great, and be prepared to wait. If you want a better viewing experience, I’d recommend going to 360 Chicago.
They also have the Signature Room on the 95th floor which is a fancy brunch and dinner spot. It looks really nice but it is fancy, they have a dress code, and dinner prices range from $30-$60 a plate.
If you’re looking to compare these two options, A Dangerous Business Travel Blog has a great post weighing the pros and cons of both Skydeck and 360 Chicago.
Terrace 16 is a rooftop restaurant and bar located in Trump Hotel. This rooftop restaurant has amazing views of the city, the Chicago River and Lake Michigan. I highly recommend this place! The views and service are incredible! I also talk about it in my Speakeasies and Bars of Chicago post. Another option would be London House . This rooftop lounge has views of the same area as Terrace 16 but the reviews are not as great. I haven’t been there, so I cannot speak to how it is.
Water Views
Chicago is right on Lake Michigan so it has amazing water views and even lake beaches! You can also take a cruise down the Chicago river for a relaxing and beautiful experience.
Cost: Free Hours: 6am-11pm
We went to this beach area to hang out and enjoy the views of the lake and the city. The weather was in the 70s the day we went so it was beautiful, and I couldn’t believe how blue the lake was! There were many people out walking, biking and even swimming. We did not swim but we did walk around and we rented some bikes to bike along the water. There is a long curled walkway near this beach that I was able to get amazing photos at! We sat around this area for hours just relaxing, and I would recommend going here when the weather is nice.
River Cruises
There are many river cruises and even lake cruises available in Chicago! We took the cheap route and used the Chicago Water Taxi! We took a cruise from Michigan Avenue down to China town and back. The cost is only $6 one way, $10 all day or $20 for 10 rides per person. We bought the all day pass for $10 and it was a great ride both ways! We went up to the top deck and enjoyed all the views.
Another option is one of their architecture river tours which gives you all the facts and history about the buildings surrounding the river. These are around $40 per person but I’ve seen great reviews on them. Next time I’ll try this (we just wanted to save a little money).
Cost: Free Hours: 10am-8pm
Navy Pier is a 3,300 foot pier along the Lake Michigan Shoreline that has a lot of shops, restaurants, and a large Ferris Wheel. It is a very popular spot to go to for tourists, and I’ve heard great things about it! Because it is a very touristy spot and because I’ve been to places similar in other cities it was on the bottom of my list, and I did not make it over to see it. Maybe next time I will go, but I would still recommend checking this place out if you are in town!
Cost: Free
There is a great walkway along the river where you can take advantage of the views, get a little exercise and walk down the Chicago river. There are a lot of restaurants and bars in this area too if you want to stop for a bite to eat or something to drink. It does get a little crowded in the summer months, but it is still a great thing to do because the views are great and its free!
Sports
We were here during baseball season and the opening of football season. We thought about going to the Bears game, but the home opener was expensive! I am going to all the baseball stadiums, so we went to both the Cubs and White Sox.
Chicago would not be Chicago without the Cubs! I highly recommend catching a game here if you can! I will go into more detail about my experience at Wrigley field in a future post.
Not as popular, but I still had to check this stadium off my list. Tickets were cheap, at only $5 per person! This is a good cheap way to spend the afternoon if you like baseball. I will go into more detail about my experience at Guaranteed Rate Field in a future post.
Sports Teams I did not get to see:
Chicago Bears – Football
Chicago Bulls – Basketball
Chicago Blackhawks – Hockey
Chicago Fire FC – Soccer
Nightlife
There is a rich nightlife in Chicago with many bars, clubs and speakeasies. Many bars stay open until 4am, so you can stay out almost all night if you want to. There are tons of bars and clubs in River North with many along Hubbard Street, you’re sure to find something. We only experienced a little bit of nightlife. For speakeasy and bar recommendations, click on my post here.
Other things we did not get to do:
Museums
Chicago has a lot of great museums! This is something I want to focus on next time I go! For a list of great Chicago museums go here.
Comedy
Chicago has a lot of great comedy shows! We just didn’t get the chance to go to one. I’ve heard great things about Second City, this is at the top of my list for next time! For other comedy options check this article out by Timeout.
Shopping
Lets face it, I did not have enough room in my suitcase for shopping even though our hotel was in the shopping district. The Magnificent Mile has more than 450 retailers along Michigan Avenue. If you love shopping, make sure you have room for your new purchases!
I hope this post gives you some ideas for things to do in Chicago!
Planning a trip to Chicago? Check out my other posts about Chicago here.
