Earlier this month, my husband and I had the chance to spend a few days together in Chicago. I was excited to see a city I’d never been to and he was excited to enjoy their style of improv. As an improvisor here in Florida, he has a few friends that way who had shows while we were there. We wanted to enjoy this trip, but at the same time we wanted to keep within our budget as we are planning a trip to Europe in the spring and didn’t want to go overspend in Chicago. Although I am by no means an expert on the city, I was able to pick up a few tips I’d like to share.
Due to the high cost of lodging in Chicago we chose to try out an Airbnb for this trip. We ended up renting a bedroom and bathroom about a 20 minute train ride out of the city for less than the cost of a sketchy motel an hour outside. The host and room were great, and even though we hit a snag before the trip the host was great and getting it figured out. Interested in trying out Airbnb? Here’s $20 off your first trip.
2. City Pass
If you’re looking to do the big attractions in Chicago (Art Institute, Willis Tower, Sci and Tech Museum, Field Museum, Shedd Aquarium) then go ahead and get yourself a city pass. this $100 ticket gets you into all 5 attractions and has a fast pass feature at several of them. They claim to have a 50% or so savings, which is a little high because you don’t necessarily need the most expensive ticket to each attraction, but in the end if you’re going to do them it really is the easy way to go. We arrived in Chicago early on a Friday morning and I wanted to go to the Willis (Sears) tower that evening. Being that it was a Friday evening the place was PACKED and had a 2+ hour wait just to get to the elevator. We were able to skip both the ticket and elevator line and get up within a few minutes which is usually $40 ticket itself. Find out more about CityPass here.
We found someone to take a photo of us with our custom message
3. Willis Tower
Speaking of Willis Tower- I wanted to share a tip I picked up. If you contact Willis Tower at least 2 days before your trip the will put up a custom welcome message up to 60 characters for free. I gave them a two hour window of when I planned to arrive and then didn’t tell my husband about it. He was so surprised to see that they knew we were coming! To set this up simply send an email to firstname.lastname@example.org. For more information go to: here.
Interested in taking in a show while you’re in town? We enjoyed a few improv shows at iO Chicago. You can check out their schedule here. While you’re in that part of town be sure to grab a bite and a craft beer at Burger Bar which is right outside the Clybourn subway station. Shows at iO vary in cost from $8 and up.
Chicago CTA station
5. Mass Transit
Speaking of subway stations, we used mass transit for every single trip except one. It was so simple getting on the train from the airport. Both the airport and our Airbnb were situated off the same train so we had no problems getting into town. The trains come very frequently and many lines run 24 hours a day so even on the late nights we had a ride home. We chose an airbnb that was less than 5 minutes from a station because we knew we’d be using it alot. This was a great decision. We purchased the 7 Day Pass which was good on all CTA trains and busses for only $28 each. Find more information on transit here.
The one car we rode in was an Uber. This was our first time using Uber so we had a ride credit which made it free! Using the app was super simple and our driver was friendly and professional. Due to the mass transit available Uber isn’t a necessity in Chicago, but It was nice to have the app and credit ready in my phone if we needed it. In case you’re wondering, we used used it to bar hop. Classy, I know. Want a free ride? Click here for a free $20 credit for your first ride. Also, Uber is so much cheaper than cabs so $20 actually goes a long way.
The view from Cindy’s
7. Chicago Athletic Association
While on our trip we met up with a friend who introduced us to the recently reopened Chicago Athletic Association Hotel. This 125 year old building once was a popular athletic association full of famous faces but closed its doors in 2007. It reopened this year as a hotel with several locally owned bars and restaurants inside. Although we didn’t get to check out the rooms, the public spaces were lovely and we thoroughly enjoyed the view from Cindys, the rooftop bar and restaurant. The building faces Lake Michigan and Millennium Park and is a great place to grab a cocktail and enjoy the view. Although the drinks are pricy, it’s worth it for view, and is much cheaper than staying the night at the hotel. We visited on a Sunday night and the place was busy, but not crazy and totally not a tourist trap. Eat dinner elsewhere and enjoy a drink and a view without breaking the bank.
The view from the door of our “chamber.”
8. Virgin Hotel
On the last night of our trip we stayed at new Virgin Hotel in Chicago. This trendy new hotel is located on the loop right in the middle of everything. The hotel is in a renovated bank building with 250 guest rooms or “Chambers.” They tried to keep as many parts of the old architecture as possible while also adding tons of swanky new updates. One of the awesome perks of staying at this hotel was the complimentary happy hour from 6-7pm. We were offered free drinks during this time in their 2nd floor bar/restaurant. This was a great opportunity to try out some fun specialty cocktails which we usually pass on. There was also a cute rooftop bar, but we didn’t get a chance to really try it out. Overall, if your interested in a fun hotel in the city I would definitely recommend this one. Because they are new, their rates are fairly low for the area. Read more about them here.
Enjoying a free happy hour drink
9. Inside Chicago Walking Tours
Whenever we visit a new city we love to do a walking tour to get to know a little about the history of the city and really get a feel for where we our. The small group settings and knowledgeable guides are great for learning more about a city. Often times they can be a little pricy for an hour or two, but we stumbled upon Inside Chicago Walking Tours via Livingsocial and tried it out. We loved our tour with Hillary and it was totally worth her rates! Although this is a new company the guide has done her research and only gives information she has verified as well as awesome notes she has come across during her research. She is also an entertaining speaker so even if history isn’t your thing you will enjoy what she has to say. Check her out, you won’t be disappointed. There is currently a deal on Livingsocial where new accounts get $10 off their first purchase of $20 or more. Click here to get that deal and then here to get 2 tickets for $20!
10. Lincoln Park Zoo
Although we didn’t get a chance to visit, the Lincoln Park zoo is worth mentioning in any post about cheap things in Chicago. This FREE zoo is located north of the city, but is easily accessible via CTA busses. Parking is expensive, so really consider taking the bus and not having to deal with the cost or traffic. It’s a great place to spend the day. Find out more here.
I hope you find these tips helpful. Please let me know if you used any of them or, if you have suggestions of your own please add them in the comments. We plan to return to the city at some point and will need new ideas!