When my college roommates and I talked about starting an annual girls’ trip tradition to reunite, we had several destinations in mind of where we wanted to go. We finally settled on going up to Chicago as none of us had ever been there before. So glad we did!
In theory, we would have all taken off a week of work, and it would’ve been this week-long celebration of where our lives have taken us, making blissful memories and not thinking twice about money. In reality, we all work and therefore could only give one weekend to each other while being budget-conscious. But, we were determined to make the most of it together, and it’s safe to say we did.
Our weekend was literally PACKED with things to do on a budget. I tried not to check my credit card while traveling, because that’s just stressful, but when I came back I was surprised that I was pretty dang close to my budget of $600. I’m happy with the amount I spent for a round trip plane ticket from NC to Chicago, 3-day parking for my car at the airport, hotel room in downtown Chicago, food, mini shopping spree at Old Navy, tourist attractions, and a 3-day public transportation pass. Read more for some tips to save money and see what you want to in a short trip to the Windy City!
1. Public Transportation Is Your Friend. Say it louder for the people in the back. Take the bus and subways throughout the city to get to where you need to go. Not only will it be easier on your feet, but you’ll get there quicker, allowing you more opportunities to see more sites! Can’t go wrong there.
The train ride from the O’Hare Airport to downtown Chicago is only $5, so it’s much cheaper than getting a taxi or Uber anyway. BUT, you should really opt for the 3-day public transportation pass for $20. This gives you access to the trains and buses around the city and to the airports.
I’ve been to large cities before, but I’ve never felt like I had to use the public transportation system for a weekend trip to see everything I wanted to see until Chicago. To me, the tourist attractions were more spread out than in D.C., for example. This is definitely a NEED if your time is limited in the Windy City.
We did take an Uber a couple of times when we were in a pinch, but luckily the rides were pretty cheap at around $7-$10 when we needed them, so it didn’t break the bank when we all split the fee.
2. Prioritize the attractions you want to see, and don’t be afraid of kicking some off your list. The reality for 48 hours in a big city is that you aren’t going to be able to do every single thing all the blogs say are “MUST SEES” in Chicago. Make a list, and don’t be upset if you have to cut some things out!
We opted to stay away from the museums for this trip. I was the only one out of all four of us that really wanted to see the Field Museum of Natural History as I heard it was awesome. Then, I found out it was $36, and museums typically take longer to walk through to really get your money’s worth. So we booted that from our list.
We chose to focus on the free attractions and then pay for the ones we REALLY wanted to do. The free attractions high on our list were Millennium Park (where the bean is), Buckingham Fountain, The Magnificent Mile, and Wrigleyville. These were located in various places and you could choose to buy things, but you didn’t HAVE to. We got all of the tourist-y photos we wanted and saw what the hype was about at each of these places.
Worth paying for in our opinion, the Navy Pier and the Skydeck were the tourist traps we felt like we needed to do. We rode the big Ferris Wheel ($15) that overlooked the water and the city and just walked around the Navy Pier. We didn’t shop at any of the shops, which is something we all said we wished we would’ve taken the time to do. We did the Navy Pier during the evening close to sundown. This is the time to go! It wasn’t super crowded, and watching the sun go down while overlooking the water and city was beautiful.
The Skydeck for us was a must. You see all these cool pictures people take with the city all around them and beneath them while being SUPER high up, and we just felt like it was worth the $23 to do. Unfortunately, it was raining all day long the day we went. Literally, all day, so the visibility for us wasn’t the greatest. The workers even warned us “NO VISIBILITY and NO REFUNDS,” but we went anyway.
It actually turned out to be awesome because we didn’t have to wait in line. Typically, this takes about 2-3 hours of waiting in line to do/see, but we went straight up to the top with no wait. The clouds ended up parting while we were up there and we still got some good views! This should definitely be on your list, but make sure you plan appropriately time-wise!
3. See a show, but don’t pay full price. If you’re into comedy shows and laughing, The Second City needs to be on your list. The tickets CAN be pretty pricey, and super popular shows sell out fast. If there’s a specific show you’re wanting to see, especially if it’s on the mainstage, I’d check times and availability early on and hop on a ticket ASAP.
If you’re like us and just want to see a funny show but weren’t going there with a specific show/comedian in mind, your options are pretty broad. We ended up seeing “She the People” in the UP Comedy Club at 11 p.m. They do have afternoon shows at a cheaper price, but we opted for the late night showing to be sure it didn’t dip into our time to visit all of the other attractions we wanted to see.
We were tired, but I’m really thankful we did it this way. It optimized our time to see more of Chicago, and once the show started, we forgot we were tired in the first place! Seriously, this show is AWESOME, especially for a girls’ trip.
Normally, when I look online to see tickets for “She the People,” general admission is $31. Don’t buy it for full price! Check out Hot Tix either online or in person at one of their downtown locations to buy your ticket. It’s cheaper, and the employees are super helpful, assisting you in picking out the show you’re looking for!
We ended up paying $20.20 for our general admission tickets vs the original $31. The woman that helped us also talked us through several other options we were thinking about as well as up-to-date information on what was currently sold out. I’m personally glad we talked to the employees in person to decide on a show that worked best for us. Less time online researching shows, more time exploring Chicago!
4.Pizza and hot dogs really aren’t that expensive. Food is definitely where I spent the bulk of my money while in Chicago. Even though Chicago as a whole was more expensive than the south, the food wasn’t as bad cost-wise as I thought it’d be.
It’s such a tourist thing, but whatever. Eat the dang deep dish pizza and Chicago dog. It’s yummy and relatively cheap. We headed to Pizano’s Pizza and Pasta for our deep dish. They have multiple locations in Chicago, and the food is GOOD, y’all. Like really good and for good prices! You really can’t go wrong.
Because we were coming back from the Navy Pier, we stopped in at the State Street location to grab some dinner on our first night in the city. The restaurant itself is a little cramped with tables really close together, but it actually made the atmosphere more enjoyable, surprisingly. It was loud enough that we weren’t being obnoxious with a normal it’s-been-a-long-time-let’s-catch-up-about-everything conversation, but not so loud that you had to yell get your story heard across the table.
We ended up ordering two medium pizzas – one deep dish pepperoni and one thin crust veggie supreme. This was PLENTY to fill all four of us up and have some leftover. Split four ways, the food ended up being around $11-$12 each, which would be a normal price I’d find at any local restaurant here in NC. I was happy with that price and the food. Highly recommend!
After we finished up at the Willis Tower visiting the Skydeck Saturday afternoon, we walked over to Union Station and grabbed a Chicago char dog at Gold Coast Dogs, and the food was pretty dang good. Now, I’m of the mindset that it’s really hard to mess a hot dog up, but that it’s also hard to get a hot dog to be above average and really stick out.
The char on the dog could have been a little more done and the poppyseed bun could’ve used a quick toast, in my opinion, but overall the hot dog was yummy. If it wouldn’t have been pouring rain on us all day Saturday, we might have tried to find another restaurant close by, but we rolled with the punches, and it was a good choice for us!
Plus, to our advantage, they had a special where you got a Chicago Style Jumbo Char Dog with a Jumbo fry and drink for less than $9. It was a lot of food for not a lot of money, and it took care of another bucket list item for us. Keeping our cost low while eating good food? YASS.
5. Stay downtown, but don’t be too picky. When we were choosing a hotel, we wanted it to be cheap enough that it didn’t break the bank, nice enough that we weren’t grossed out to sleep there, and downtown, close enough to all of the attractions we wanted to see.
It took some searching and comparing from all four of us before we finally landed on the Best Western River North. This ended up being a great choice for us as it was close to both bus and train stations and within walking distance of the Magnificent Mile (and technically walking distance of other things, but taking the bus is faster).
Split between all four of us, we paid $112.50 each for two nights in downtown Chicago. Not too bad, I’d say. This was cheaper than any other hotel or AirBnB that we could find for the location. It was also important to us that we were in a good part of town, considering it was just going to be four young women on our own and we knew we’d want to stay out late at least one of the nights.
Make no mistake, we slept in full size beds and the room was pretty small. There was only one sink in the bathroom, no full size mirror, and not enough towels to go around. But, we knew we’d really only be sleeping here and maybe coming back once during the day if we needed a break (which we did at one point!).
If we wanted to spend a little more money, we definitely could have and would’ve had much nicer amenities, but for the price we were willing to pay, the Best Western served all of our needs well. You’d definitely be able to decrease the cost by quite a bit if you stay outside the city, but, again, we chose convenience as an important factor in where we wanted to be and what we were willing to pay for.
All in all, we had such a fun trip. Lots of food, walking, talking, laughing, chocolate, and catching up happened. It was relaxing while still being busy. I’m so glad we took the weekend away together to reunite. It’s exactly what we needed, and we decided we’d do our best to make it a yearly tradition. We’ve got a few ideas on our list, but no final decision on where our next trip will be!
Where should we go next?