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The Best Of Chicago In A Day For Less Than $50

We’ve got the best recommendations for how you can spend a full day enjoying the best of Chicago for under $50.

Chicago is the jewel of the Midwest, inviting travelers worldwide to experience its modern-day skyscrapers, picturesque beaches, world-class art, and vibrant culture. And the best part about traveling to Chicago is that it doesn’t have to break the bank! We created a list for you to see the best of Chicago in a day for under $50.

While it’s possible to have a lavish, luxury holiday trip to the city, it can be excessive when you realize all of the things that you can enjoy for a reason. We’ve got the best recommendations for how you can spend a day enjoying the best of Chicago for under $50.

The Best Breakfast: Wildberry Pancakes & Café

(Source: Wildberry)

Wake up early for a chance to enjoy one of the hottest breakfast spots in town: Wildberry Pancakes & Café. You know you’ve stumbled upon a gem if you see the locals frequenting it, so grab a seat and get ready to dig in!

Wildberry Pancakes & Café is an American-style café serving up all of your traditional favorites. However, it’s famous for its specialty pancakes that you can’t leave without trying! The signature Wildberry Pancakes are the obvious choice. Accompany it with a glass of freshly squeezed orange juice, and you’ll be all set for a long day ahead of exploring the Windy City.

You can find Wildberry Pancakes & Café in downtown Chicago, a short walk from many hotels in the area.

Cost: $10.95 for pancakes, $3.50 for orange juice

The Best Sausage: Jim’s Original

(Source: Jim’s Original)

A best of Chicago list wouldn’t be complete without a sausage spot. Chicago is known for its sausage sandwiches, and speaking with the locals will point you all around the city when trying to find the best restaurant. Skip the fine dining establishments because the local spots will give a much more authentic dining experience.

Thanks to the diverse cultural groups that settled in the city throughout history, you now have a chance to experience traditional sausage dishes from around the world, like Germany, Poland Italy, in one place.

Head over to the beautiful campus of the University of Chicago to find Jim’s Original, where its stood since 1939. The Maxwell Street Polish sausage is a must-try.

Cost: $4.70

The Best Pizza: Giordano’s

(Source: Giordano’s)

Step aside New York because Chicago’s famous deep-dish style pizza might give it a run for its money. This incredible creation seems too good to be true with every savory bite. And we couldn’t have a best of Chicago list without featuring Giordano’s.

From humble beginnings on the Southside in 1974, Giordano’s helped create the craze around Chicago-style pizza. While they have added several new locations, nothing compares to tasting at the original shop.

Visit Giordano’s first location on N Rush St., where it perfected the art of the Chicago-style pizza: a thick, deep dish with a crispy crust and topped with cheese and toppings. 

Cost: $10.85 for Individual sized with one topping 

Best Walk: Chicago Riverwalk

river between trees and city skyscrapers
(Photo by heather bozman on Pexels.com)

The Chicago River runs directly through the city to connect the local canals to Lake Michigan. It forms a spectacular waterfront area full of skyscrapers, bridges, and more.

Before, the only way to experience the riverfront was via a river cruise, which is still popular but can cost over $20 for one ticket. But thanks to the Chicago Riverwalk built-in 2001, it’s a better alternative, and best of all, free! You can’t see the best of Chicago without a stroll through the Riverwalk.

The Riverwalk extends for 1.25-miles along the riverfront with a paved pedestrian walkway lined with shops, restaurants, and bars. It’s an excellent place to people-watch or hang out for date night.

You’ll get the same great views of Chicago’s skyline as paying to take a cruise, but without the fee.

Cost: Free

Best Rooftop Bar for Drinks: Cindy’s

Cindy's Rooftop
(Source: Cindy’s)

You’ve spent plenty of time exploring the streets of Chicago from the ground level, surrounded by towering skyscrapers. Well, now, it’s time to get eye level with these massive buildings. So what better way to enjoy the skyline than with a refreshing cocktail?

Chicago is full of rooftop bars, but none compare to Cindy’s Rooftop, located at the top of the Chicago Athletic Association Hotel. You’ve never seen a place so stylish, boasting a contemporary décor and lively atmosphere—and that’s just the inside.

Walk over to the bar for a handcrafted cocktail before stepping onto the outdoor deck to be awed by views of Chicago stretching out to Lake Michigan.

Cost: $16 per cocktail

Best Way To Get Around: L Train

aerial photo of railway lines
(Photo by Leon Macapagal on Pexels.com)

Taking public transportation is a pleasant surprise in Chicago. Chicago’s L-train is not only functional, but it serves as a self-guided tour of Chicago.

Every day, over three-quarter million people ride on Chicago’s rail system. But what’s a daily commute for them will be a fantastic sightseeing tour for you.

Chicago’s L-train is an outdoor sky rail servicing The Loop downtown. This loop encompasses many of Chicago’s iconic landmarks, like the Willis Tower, the Art Institute of Chicago, and Millennium Park.

While you can use the train for getting around, you can also purchase one trip and ride the entire loop.

Cost: $2.50 per ticket

The Best Place to Enjoy Outdoors: Millennium Park

The best of Chicago Millennium Park
Photo by Gotta Be Worth It on Pexels.com

The hustle and bustle of Chicago may be overwhelming for some people, and you may need a break from trekking around town. Opt-out of returning to your hotel and instead set your destination to Millennium Park, Chicago’s most visited attraction with 25 million visitors every year.

Millennium Park is a massive urban park located in the heart of Chicago’s downtown loop. Before grabbing a seat, check out the famous Cloud Gate sculpture, a reflective public art installation piece that many refer to as “The Bean.” The Bean has a unique concave shape that distorts the view of Chicago’s skyline.

Check the schedule before you go because you could check out one of the free annual festivals held at the park.

The Best Skyline View: Buckingham Memorial Fountain


Since a trip to the top of the Willis Tower Observation Deck would eat up too much of your budget this trip for one activity ($30 per ticket), there are better ways to get a great view and even more if you stick around until the nighttime. This is our favorite place on the best of Chicago list.

Join the hundreds of thousands of people that visit the Buckingham Memorial Fountain every year. Located in Grant Park, the decorative Beaux-Arts style fountain is one of the largest in the world. It stands as the centerpiece of the park, where you’ll have a spectacular view of Chicago’s entire skyline.

It has a daily water show between April and October with water shooting up to 150-feet into the air and set to music. Colorful lights illuminate the fountain at night.

Cost: Free

Best Place To Relax: Chicago’s Beaches


When it comes to Chicago, most people don’t often think about beaches. But, surprisingly, Chicago’s shoreline extends for 22-miles along the Lake Michigan coast. That means it’s plenty of places to sunbathe or go for a dip in the lake.

If you’re traveling to Chicago during the summer, the beach is an excellent way to enjoy Chicago on a budget because they’re free to visit!

Chicago’s best public beaches are North Avenue Beach, Montrose Beach, and Ohio Street Beach. These beaches all have soft, golden sands that slope gently into the cool freshwaters of Lake Michigan. Don’t forget your towels and sunscreen!

Cost: Free

The Windy City Awaits

Are you excited yet to conquer this best of Chicago list? Then, get ready for a long day of fun as you fill up your itinerary with exciting activities that give you the authentic best of Chicago experience on a budget.

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