Over the weekend, Michael and I spent 24 hours in Chicago with my best friend and her fiancé. There were a million reasons why this trip was so special – we celebrated Michael’s birthday, the two year anniversary of our first date, Michael meeting my lifelong best friend (Rebekah) and her fiancé, and so many more things. This was my second time to Chicago and Michael’s first, so we really packed in as much as possible since we were there for such a short time. I’ll walk you through our 24 hours in Chicago and spill all the deets on where to stay, what to eat and everything you need to do during a quick budget friendly trip to the windy city.
When I travel, I like to enjoy as many local experiences as possible. I don’t want to spend all of my money on 5 star Michelin restaurants, but I don’t want to eat at McDonalds or tourist traps either. I love choosing budget friendly options that still provide incredible memorable experiences. I apply that to where I choose to eat, the hotels I pick and the activities I plan. If you are traveling to Chicago and still want to keep it affordable, this 24 hour budget friendly Chicago itinerary is for you.
Breaking down all of the meals we ate and where they are located. Trust me, you won’t be leaving Chicago hungry!
We started our trek on a Friday night and drove from Grand Rapids to Chicago. It was a quick 3 hour drive into the city and obviously, our first stop upon arrival was for pizza. Michael has never had deep dish, so we scouted out the best in the city while driving to Chicago, read reviews and finally decided on Nancy’s Pizza. Rebekah and Andy are vegan, so they found a totally vegan pizzeria so they could enjoy deep dish as well. They chose Kitchen17.
Both restaurants had our pizzas ready for us in about 30 minutes and they each cost about $35. Nancy’s Pizza and Kitchen17 are both located on North Broadway Street, so it made it extremely convenient for us to run in and grab our pizzas. We packed them up and drove to a nearby park along the Lakefront trail and demolished the pizzas so fast. I’m not vegan, but try to avoid dairy as much as possible (just doesn’t sit well with my digestive system or my skin), so I had two slices from Kitchen17 and a few bites of Michael’s pie from Nancy’s. As a non-vegan, I am happy to report that Kitchen17 tasted basically identical to Nancy’s non vegan deep dish. They were equally cheesy and flavorful. I’d recommend both places!
Coffee was obviously an important start to the day, and we hit up Metric Coffee for our morning caffeinating. Metric is a little bit outside of the city located on W Fulton St, but it’s totally worth the few extra minutes it takes to get there. Order the oat milk latte light on the vanilla or the iced matcha.
For our breakfast/brunch, we chose a vegetarian/vegan friendly option – Handlebar, located on W North Ave. Regardless of your dietary preferences, Handlebar is a must when visiting Chicago for a quick trip. They have been serving up drool worthy comfort food since 2003. All seating is outside on their back patio. It is quiet, private and so dang cute! We had incredible weather, so sitting out in the morning sun was an amazing start to the day.
As far as Handlebar recs, I’d order the Diablos, Vegan Dream Mac and Roasted Mushroom Omelet again and again and again. Rebekah and Andy split the vegan chimichanga and it was the size of a newborn baby – you will not be leaving hungry, that’s for sure! We each got an entree (which were massive portions) and three sides to share. The total bill for everything was $67. Not bad for the amount of food we ate and had leftover to take home! Definitely a win in my book for the budget and for my belly.
By the time 3pm rolled around, we were ready for our mid-day sweet treat. RealGood Stuff Co. on Wells St is a healthier option with dairy free soft serve and nutritious made to order bowls. Get the Oreo NoYo (their dairy free version of soft serve) with the vegan cookies and chocolate fudge. UNREALLLLLL. You guys know I am an ice cream fiend, so finding this plant based option was one of the best parts of my day!
For our final dinner in Chicago, we got takeout from DAO Thai located on E Ohio St. If we had had more time we definitely would have eaten at the restaurant, but wanted to get home so opted for takeout instead. DAO has the cutest fluffy cushions and cozy seating arrangements to enjoy when eating in. I had the Pad Woon Sen, Michael got Pad Thai and Rebekah and Andy split the Panang Curry with Tofu. Everything was to die for, and Michael said the Pad Thai was tied for the best he’s ever had. I know, those are strong words. Don’t just take our words for it, you need to try it for yourself. DAO is also so affordable! Our total bill for three massive portions was under $40, and we all had leftovers to eat for breakfast the next day. Any time I can have leftover Thai food, I am one happy girl. DAO did not disappoint!
Chicago is a big city and sometimes walking is just too much and ordering an Uber is just too inconvenient. All over the city are racks of Divvy bikes – a secondary chain of Lyft. Download the Divvy or Lyft app, scan your bike’s code and start exploring the city on the go! I seriously cannot recommend these bikes enough. Hop on at Navy Pier and ride to Millennium Park. Ride along the Lakefront Trail – it will only take about 15 minutes and costs $3. Riding the Divvy bikes along the Lakefront trail might be the most memorable part of my Chicago trip. The sun was shining, the sky was so blue, the water was sparkling and I was surrounded by three of the people I love the most. It was literally something out of a movie, that’s how magical and beautiful it was.
We ended up using the bikes three different times during the day as we decided where we wanted to go. After you rerack the bike, the app will tell you how far you rode and how long you spent on the bike. We ended up coving about 13 miles total and saved ourselves so much time and money than if we had walked or gotten an Uber. I’m obsessed with these bikes for a budget friendly way to explore the city!
If you are traveling to Chicago when the weather will be enjoyable, you HAVE to visit some of the parks. For such a big city, Chicago has a surprising number of beautiful spacious parks – 600 to be exact. I also noticed that it is one of the cleanest cities I’ve visited. Especially during COVID times, and with so many restaurants only doing takeout, enjoying your meals in a park is the way to go. We ended up eating our Thai food in one of the dog parks near Navy Pier. It was so cute watching all the pups and enjoying DAO’s cuisine. If the weather is good, a walk along the Lakefront trail is a great way to spend some time. It is absolutely gorgeous and there are so many fun sites to see along the way.
When it comes to tourist attractions, they usually aren’t my favorite. I do think everyone should see the big tourist attractions once, but I wouldn’t waste my time there. Since it was Michael’s first time in Chicago, we did make our way to Millennium Park to see the Bean and spent some time near Navy Pier (it was closed off due to COVID, but Michael flew his drone over the pier so he could get the general idea).
If you’re a plantaholic like me, there are various garden centers and plant shops to check out around the city. They all have beautiful unique plants that you can buy as a living souvenir from your trip. My favorite stop was Chicago Plants on W North Ave (just a few steps from Handlebar and the perfect place to stop in after a yummy breakfast). I’d also recommend Garfield Park Conservatory for the most beautiful tropical FREE experience.
You’re going to need a place to sleep and in my opinion, when only having a short time in the city, getting a bougie hotel room isn’t worth it to me. I like having a clean and cozy hotel room, but I won’t ball out for something luxurious if I’m going to be spending less than 12 hours in the hotel. We stayed at the Freehand on E Ohio St in the Superior King room. We booked the rooms less than 48 hours in advance and paid less than $110. The rooms are clean and comfy, but nothing over the top. The Freehand has eclectic décor, a spacious lounge area and free parking, so it was perfect for what we were looking for. It is also located in a convenient location, so going back and forth to the car to drop things off as needed was super easy. The staff at the Freehand is SO kind and friendly. I would definitely stay there again during a quick trip to Chicago!
This short 24 hour Chicago trip was so quick, but packed full of amazing memories, delicious food and unforgettable experiences with my best friends. I absolutely love Chicago, and look forward to going again and adding more recommendations to this list. Have you been to the Windy City? Share your favorite Chicago recs with me in the comments, or over on Instagram. I’d love to hear more about your travel experiences!! Stay tuned for a mini Grand Rapids guide, coming soon!
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Hi there, I'm Anna
Brunette Collective is a lifestyle blog focused on creating happiness through an intentional life, founded by Anna Fenstermacher.
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