The Best & Cheapest Way To Spend Two Days In Chicago

If you follow me on Tiktok or Instagram, you might know that I recently took a spontaneous road trip to Chicago in hopes of finding the best deep dish pizza. I did not find the best deep dish, but I did find the best pizza ever, and you can read more about that here. Today I’m going to let you in on everything else we did on our 24 hour trip & how much the trip cost.

Did you know there are free zoos?

While there aren’t very many of them, Chicago’s Lincoln Park is home to one! This zoo was smaller since it’s free but it still featured Lions, Zebras, Giraffes, Flamingos, Penguins, Monkeys, Polar Bears, and more! We had a great time walking through the park and exploring the zoo and got to see some pretty cool exhibits. It was nice to do a free activity since this trip was last minute, and the size makes it easy for families with small children to see the entire zoo. We walked from our accommodation, so we didn’t pay for parking but I know the zoo parking area was not free. They do have donation boxes to help support the zoo, and we recommend giving what you can to help keep the zoo affordable for all!

Lunch at the Timeout Market Is For The Indecisive

If you often crave multiple types of food at one time and wish you could get a dish from 4 of your favorite places to make a meal, the Time Out Magazine Market has your back! With 21 different places to eat or grab a drink under one roof you can satisfy your most unique cravings from donuts to sushi, to soul food and sandwiches. They also hold special pop-up events and if you know me you know I have been a massive Taylor Swift fan since I was 13 and she released her debut album. So of course we had to go to the “All Too Well” pop up sandwich shop. Was it more expensive than it would have been in Ohio? Absolutely it was, but it was also worth it because we shared the sandwich so we could grab donuts from Firecakes. FYI – You can find the All Too Well sandwich shop, along with Firecakes and many of the other shops, on their own throughout Chicago.

The Bombay Chulet Sandwich – All Too Well
Pistachio Old Fashioned & Churro Donuts – Firecakes

Getaway Chicago Changed Our Mind About The Hostel Experience

Andy and I try not to go through life letting our preconceived notions about things rule our experiences. In our heads hostels were cheap and dirty and not very safe. Maybe some of them are, but our first experience with Getaway Hostel in Chicago was the opposite of our expectations. They had great google reviews, no mentions of bed bugs (a great fear of mine), and were consistently labeled clean. They also offered a continental breakfast for $6, which you can’t opt out of, but it was $6 per bed not per person. I booked a private room with a shared bathroom, think college dorm style, so that we weren’t totally bunking it with a bunch of strangers for our first time. They also offer parking behind the building, which looked safe and well-lit. The room cost us $105 after taxes & fees which was $100 less than anything available at the time of our trip. Parking was $32, which is a little steep but we could leave our car there after checkout if we wanted more time to explore the area. Additionally, it was located in the Lincoln Park neighborhood and we had tons to do, including the zoo, within walking distance. Our room, the lobby, and the bathrooms were clean and looked up-to-date. The continental breakfast offered the typical cereal, waffles, toast, etc. The bed and pillows were not the most comfortable ever, but for $85 before taxes we weren’t expecting more than a place to sleep, and we did get a decent night’s sleep. We would recommend this Hostel if you’re passing through Chicago for a night or two and want to sleep on the cheap without sacrificing cleanliness!

The Getaway Hostel Chicago Lobby
Our Room ft. Andy hiding poorly for my video.

Last But Not Least – Millennium Park & Navy Pier

I’m not sure it’s physically possible to visit Chicago without visiting Millennium Park & Navy Pier. First thing’s first – If you want to save some money on the outrageous parking fees book ahead of time (as soon as 5-10 min early) on SpotHero. When we booked, we paid $12 for parking that would have been $27 if we paid at the gate. If you’re an ice cream fan there is a Ben & Jerry’s Scoop Shop on the pier, which was a nice treat while we walked around. There is also a City Mini Golf course featuring a Chicago hot dog as the 18th hole in Millennium park on the opposite side of Could Gate (A.K.A The Bean). The best part is exploring the park & pier is free and family friendly. Certain areas are also dog friendly!

Special mention to Hook & Ladder bar. They had a laid back atmosphere, could make you just about any drink, and have great specials (plus a discount for using cash). Highly recommend it if you need a place to hang out and have a drink between adventures.

That wraps up our 2 days (really 27 hours) in the windy city! Our total expenses for this trip after gas, food, accommodations, parking, snacks, drinks, etc. was $372.31. Not our cheapest trip- but not bad for 2 tanks of gas, a place to stay, 4 meals and planned in under 48hrs. Parking really took it out of us – totaling $64, if we had discovered SpotHero sooner in the trip we likely could have saved half of that! Even with that expense, our budget was $400 so we stayed in budget which is always a win!

If you are tired of getting bogged down by the logistics of planning your road trip, you need to sign up for a trip created just for you by me! I have an Adventure Quiz to help get us started and I can have a trip put together for you in as little as 4 weeks. If you’re wanting to go on a short spontaneous, or even surprise trip, reach out to me at [email protected] I may be able to put a fun trip together for you quickly depending on availability!

-Taysia