There’s a common misconception that visiting Chicago has to be expensive. Between the famous deep-dish pizzas, rooftop bars, architecture cruises, and world-class museums, it’s easy to assume you’ll need a generous budget to enjoy the city. But after spending a few days here, I wanted to see if that was actually true.
So, I set myself a challenge. Could I experience some of Chicago’s most iconic food, explore some of its best neighbourhoods, and still stay within USD 50?
The slightly ridiculous part is that this challenge was entirely my own idea. I could have made it a USD 100 challenge and made life much easier, but where’s the fun in that?
As it turns out, Chicago on a budget is far more achievable than I expected. Here’s exactly how I spent my USD 50, what I ate, where I went, and a few extra free activities I’d recommend if you’re planning your own trip.
My Chicago on a Budget Breakdown
Here’s exactly where my money went throughout the day.
- French Toast (Yolk): USD 6.00
- Coffee: USD 4.75
- Plant-Based Burger + Cheese (Small Cheval): USD 15.38
- Personal Deep-Dish Pizza (Lou Malnati’s): USD 13.25
- Dairy-Free Ice Cream (The Ice Cream Social): USD 9.20
Total Spent: USD 48.58
Money Left Over: USD 1.42
The best part? I managed breakfast, lunch, dinner, dessert, and spent the rest of the day exploring some of Chicago’s most famous attractions without going over budget.
Can You Really Visit Chicago on USD 50?
I genuinely wasn’t sure this challenge was possible. Chicago has a reputation for incredible food, but it also has a reputation for being expensive. The trick was choosing my meals carefully, walking between attractions instead of using transport, and taking advantage of the many free places the city has to offer.
By the end of the day, I’d eaten four times, explored some of Chicago’s most iconic neighbourhoods and attractions, and still stayed within my budget. If you’re willing to mix affordable meals with free sightseeing, it’s entirely possible to enjoy Chicago without spending a fortune.
The Best Budget-Friendly Restaurants in Chicago
Breakfast at Yolk
I quickly realised breakfast would set the tone for the rest of the challenge. If I spent too much here, I’d probably be surviving on snacks by dinner.
Instead of ordering Yolk’s famous full serving of French toast, I spotted what felt like the perfect budget hack. You can order a single slice for just USD 6, and considering American serving sizes, it turned out to be more than enough.
It arrived topped with fresh berries, whipped cream, and syrup, and honestly tasted more like dessert than breakfast. It was incredibly soft, fluffy, and one of the best value meals I had in Chicago.
The coffee, on the other hand, was almost as painful as airport coffee prices. At USD 4.75, it wasn’t exactly cheap, but I simply can’t function without coffee.
Lunch at Small Cheval
For lunch, I headed to Small Cheval, one of Chicago’s best-known burger restaurants. Since I’m pescatarian, I skipped the famous beef burger and ordered the plant-based version instead.
With cheese added, lunch came to USD 15.38.
The burger itself was really good. It came with lettuce, tomato, onions, pickles, Dijon mustard, and perfectly melted cheese inside a soft, toasted bun. Was it the best burger I’ve ever eaten? Probably not. Would I happily eat it again? Absolutely.
The unexpected highlight of lunch wasn’t actually the burger. It was spotting Steve Carell casually walking into the restaurant. I left him alone to enjoy lunch with his family, but internally, I was having a complete fan moment.
Dinner at Lou Malnati’s
You simply can’t visit Chicago without trying deep-dish pizza. I headed to Lou Malnati’s, one of the city’s most iconic pizza restaurants.
One thing worth knowing before you visit is that deep-dish pizzas take time. During busy periods, there can be a wait for a table, followed by another 45 to 60 minutes for the pizza to cook. Luckily, you’re able to pre-order your pizza while waiting, which saves plenty of time.
I ordered a personal cheese pizza with the buttery crust upgrade for USD 13.25.
The crust was rich and flaky, the tomato sauce was beautifully balanced, and there was no shortage of cheese. It was genuinely delicious.
That said, if I had to choose, I actually preferred the deep-dish pizza I’d previously tried at Pizzeria Uno. I found it a little chunkier, more filling, and slightly better value.
Dessert by the River at The Ice Cream Social
After dinner, I still had enough left in the budget for one final treat. Using Google Maps, I found a small riverside ice cream shop, The Ice Cream Social, overlooking the Chicago River.
I ordered a dairy-free mango and passionfruit ice cream topped with fresh strawberries for USD 9.20. After walking around the city all day in the summer heat, it was exactly what I needed.
Sometimes the setting makes food taste even better, and eating ice cream beside the Chicago River was the perfect way to finish the challenge.
The Best Places in Chicago I Visited Without Spending a Fortune
One thing that surprised me most about Chicago was just how many incredible places you can enjoy completely free.
Chicago Riverwalk
If you only have time for one free activity in Chicago, make it the Riverwalk. Stretching alongside the Chicago River, it’s one of the most enjoyable places to simply wander.
Historic buildings sit beside modern skyscrapers, boats glide beneath the city’s famous bridges, and cafés spill onto the waterfront. On a sunny afternoon, the atmosphere is fantastic.
I ended up spending far longer here than I’d planned because there was always something happening.
The Magnificent Mile
Even if shopping isn’t in your budget, the Magnificent Mile is worth visiting. Chicago’s famous shopping district is lined with department stores, luxury boutiques, and flagship retailers, making it one of the city’s busiest streets.
I may have slightly sabotaged my own “budget traveller” reputation by buying a pink dress from Nordstrom, but thankfully, that wasn’t included in the USD 50 challenge. Window shopping is completely free, after all.
River North
I stayed at the Acme Hotel in River North, and I couldn’t have picked a better location. Everything felt within walking distance, including the Riverwalk, Millennium Park, and the Magnificent Mile.
If you’re visiting Chicago without a car, staying somewhere central like River North can actually help you save money on transport.
Free Things to Do in Chicago
One of the reasons I love challenges like this is that they remind me that travel doesn’t always have to be expensive. I truly believe travel should be accessible to everyone, and thankfully, some of Chicago’s best experiences don’t cost a thing.
Walk Through Millennium Park
Home to the famous Cloud Gate sculpture, better known as “The Bean,” Millennium Park is one of Chicago’s must-visit attractions. It’s the perfect place to relax, people-watch and enjoy the city’s skyline.
Visit Lincoln Park
Lincoln Park offers beautiful walking paths, gardens, beaches and plenty of green space. If you’re visiting during the summer, it’s a lovely place to escape the busy streets.
Explore Navy Pier
Even if you don’t buy tickets for the Ferris wheel or boat cruises, Navy Pier is a fun place to wander. There are regular performances, waterfront views and plenty of places to sit and enjoy Lake Michigan.
Watch the Chicago River Bridges Lift
If you’re visiting during bridge lift season, watching the city’s historic bridges rise to allow boats through is surprisingly fascinating and completely free.
Wander Around the Chicago Cultural Centre
Many visitors don’t realise the Chicago Cultural Centre is free to enter. Inside you’ll find beautiful architecture, rotating art exhibitions and one of the world’s largest Tiffany stained-glass domes.
Tips for Visiting Chicago on a Budget
A few things helped me stretch my budget further throughout the day.
- Stay in a central neighbourhood so you can walk to most attractions.
- Look for smaller menu options rather than ordering full portions.
- Carry a reusable water bottle instead of constantly buying drinks.
- Explore free attractions between meals rather than paying for tours.
- Walk as much as possible because many of Chicago’s main sights are surprisingly close together.
Is Chicago Worth Visiting on a Budget?
Visiting Chicago certainly can be expensive, but after spending the day exploring, I realised you don’t need a huge budget to enjoy everything this incredible city has to offer. Between the affordable food, walkable neighbourhoods, and countless free attractions, Chicago proved to be far more budget-friendly than I expected.
If you’re planning your own trip, I hope this guide shows that experiencing Chicago doesn’t have to cost a fortune. Be sure to check out more destination guides here on Travel For Phoebe blog, and head over to my YouTube channel, where you can watch my full USD 50 Chicago Food Challenge and come along for the adventure.
Have you ever challenged yourself to explore a city on a budget or discovered an amazing bargain while travelling? I’d love to hear your stories and tips in the comments below!