Chicago on a Dime: How to See the Windy City in 4 Days Without Breaking the Bank

The Windy City is known for many things - its stunning architecture, vibrant arts scene, and intense weather - but being cheap isn't one of them! Even with rising city costs, Chicago is not to be missed and has so many gems to uncover. With plenty of planning, you can uncover those gems without breaking the bank! In this post, I'll share my tips and a budget-friendly itinerary for first-time visitors looking to explore the city!

Accommodations

There are so many fantastic hotels and areas to choose from in Chicago that it can be overwhelming! For a dash of history with a side of supernatural mystery I opted for the Congress Plaza Hotel. This hotel is well-known for it's ghost stories and classic Chicago charm. The Congress Plaza Hotel was also a famous stop for many of our U.S. Presidents. If spooky bumps in the night is not your cup of tea. I also recommend Freehand Chicago for great location and very affordable private rooms and hostel-style accommodations as well!

Chicago Transportation

Chicago has plenty of great transportation options to choose from:

• Chicago Transit Authority - This system covers the "L" Trains and the Bus system in the city. I used public transportation my entire time in Chicago! You can get a Ventra Card for access to everything. You can pay $2.50 for a single ride or get unlimited ride passes which is what I did (pricing info here). I used my Apple Maps and swapped my settings over to public transportation to get step by step instructions on navigating the CTA!

• Metra - If you plan to explore outside of downtown, you can use the Metra trains to explore the suburbs.

• Divvy Bike Share - Chicago has a bike-sharing program with plenty of stations throughout the city. Single rides start at $3.50, or you can purchase a day pass!

• Taxis and Ride-Sharing (Uber and Lyft) - These are widely available throughout the city but can be more pricey to get around. Save these for late-night adventures or when you're too stuffed with deep-dish pizza and Chicago dogs to walk!

• Walking - Chicago is a very walkable city! Especially if your hotel is in downtown areas like the Loop, River North, and the Magnificent Mile.

• Water Taxi - Take the Chicago Water Taxi for a more scenic route to get to Chinatown, Riverwalk, and Michigan Avenue.

Day 1: Downtown and Lakefront Adventures

Morning:

Start the day bright and early at Millennium Park before the crowds get there by seeing the iconic Cloud Gate sculpture ("The Bean") and Crown Fountain. Take a look at their calendar as there are often free events happening in the park!

Next, stroll over to nearby Grant Park and admire the beautiful Buckingham Fountain, one of the largest in the world. From here you can get beautiful views of the city skyline and Lake Michigan!

Afternoon/Evening:

Head to the Chicago Riverwalk to stop for a quick meal or drink in the riverside bars and cafes.

Catch a game or take a tour of the iconic Wrigley Field! Wrigley is the second-oldest active MLB ballpark behind Fenway. Even if you're not a sports fan, the Chicago energy here is contagious!

Day 2: Lincoln Park and Comedy

Morning:

Take the time to explore the Lincoln Park Zoo, one of the oldest zoos in the U.S.! It's a free zoo to explore and worth a visit to explore. While in the area you can also walk over to the Lincoln Park Conservatory to explore the gardens!

Afternoon:

Grab a quick lunch in Lincoln Park before doing an afternoon walking tour of Lincoln Park. The neighborhood has so much history to explore and there are plenty of touring groups to choose from! I took a free Blues and Gangster walking tour of Lincoln Park and absolutely loved it. It was tips-based so you pay what you think the tour is worth!

Evening:

Head to Second City for a Comedy Show! Chicago has jokes and Second City is well known as a premier comedy club with shows most nights of the week.

Day 3: Nature and City Views

Morning:

Begin your day by exploring the gorgeous Garfield Park Conservatory. The conservatory is free and absolutely stunning! The conservatory is filled with diverse plant species and beautiful displays that make you feel completely immersed.

Afternoon:

Try a traditional deep-dish pizza for lunch! I went to Lou Malnati's but there are many places in Chicago to try traditional deep dish. Just know - order less than you think you'll need because slices are huge and very filling!

After wrapping up lunch, take a Chicago Architecture Tour. I found a Groupon for this one and loved it, but there are plenty to choose from and be sure to price compare and check Groupon for best deals!

Evening:

For gorgeous city views without paying high prices, head to the Hancock Building and go up to the 95th floor to go to the Signature Room and grab a drink! For all the ladies, make sure to check out the bathrooms for even more stunning views!

End the night by taking a tour through Chicago's brutal past with a Ghost tour! I took this free Haunted History walking tour and was a big fan. It is through the same company I mentioned earlier for the tour of Lincoln Park so make sure to bring cash for tips!

Day 4: Culture and Local Flavors

Morning:

Spend your morning soaking up artistic masterpieces by exploring the Art Institute of Chicago! You can spend hours wandering through the halls of the Art Institute. I still had my Student ID with me from college and used it to snag a discount on my tickets, so keep an eye out for any discounts!

Afternoon:

If you are a big baseball fan like me head over to Guaranteed Rate Field for a White Sox game or take a tour of the stadium!

If you're a little baseball-ed out, instead opt to go to the Field Museum or Shedd Aquarium!

Evening:

Grab classic Chicago-style hot dogs at Chicago's Dog House or another popular hot dog joint before continuing along to Navy Pier where you can enjoy the views, rides, and attractions!

Chicago is an amazing city with so many sights to explore. This itinerary barely scratches the surface of all of the things to see in the city! What are your favorite stops in the Windy City? Let me know in the comments!