14 Travel Hacks to Save Money in Chicago’s Peak Season

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We’ve created a list of 14 travel hacks for Chicago’s peak season that will help you save money and still have a great time exploring the city!

Are you visiting Chicago during peak season and looking for creative ways to save money? Look no further! Chicago’s peak season can be a great time to explore the city, but it can also be expensive if you don’t know the best travel hacks to save money. 

From booking flights at the right time to finding the best deals on food, we are sure that you will find at least one travel hack that will help you make the most of your visit to Chicago without breaking the bank.

14 Travel Hacks to Save Money in Chicago

1. Consider Alternative Airports

Sometimes flying into a smaller airport that is near your destination can be cheaper than flying into the main airport. This is a travel hack that is often overlooked.

In Chicago, the primary choices are O’Hare International Airport (ORD) and Midway International Airport (MDW). Flying into a smaller airport, like Midway, is a great travel hack for flying and you will most likely find lower fares. 

2. Look for Package Deals

Packages that combine flights, accommodations, and activities can often be good value and save you money. Southwest Airlines has some of the best Chicago travel packages, so check out their rates for a bundled deal.

3. Use Public Transportation

This is my favorite travel hack when visiting large bustling cities. Chicago has an extensive public transportation system that is affordable and convenient. Consider using the CTA trains or buses to get around Chicago and save money instead of relying on taxis or rental cars.

4. Book Accommodations Outside the City Limits

While staying in downtown Chicago may be convenient, it can also be expensive. Use this travel hack to save money.

Instead of booking at a pricey hotel downtown, consider staying in a neighborhood outside of downtown, such as Rosemont or Oak Park, where you can find more affordable accommodations and still be close to public transportation.

Summer is the peak tourist season in Chicago, which means crowds and higher prices.

You should also consider visiting in the spring or fall to avoid the crowds and save money on accommodations if you prefer to be in Lincoln Park, River North, or on the Magnificent Mile.

5. Visit Museums for Free

There are lots of travel hacks that we list for our readers who love museums. For example, many of Chicago’s top museums like the Art Institute of Chicago offer free admission on certain days or during certain hours. Make sure you read these guides to learn how to get free entry.


6. Get a Chicago CityPASS

If you plan on visiting multiple sights, consider purchasing a Chicago CityPASS to see the top Chicago attractions. This pass provides discounted admission to several popular tourist destinations, including the Field Museum, Shedd Aquarium, and Skydeck Chicago while allowing you to save money on travel. 

7. See Top Attractions for Free

Chicago has many free outdoor activities that are available year-round, including visiting Millennium Park and the Lincoln Park Zoo. This travel hack will give you access to activities while enjoying the city without spending any money.

8. Pack lightly

One of the best Chicago travel hacks to save money is to pack lightly. By bringing only a carry-on bag, you can save hundreds of dollars on checked luggage fees. 

Airlines like American and United charge fees for checked bags ranging from $25 to $50 per bag depending on the route. 

By packing light, you can avoid this additional cost, especially when flying with a family or group. Instead of checking multiple bags, try to limit your belongings to just one carry-on bag to save money on travel.

travel hacks chicago's peak season

9. Bring Your Snacks

Buying food and drinks at airports and on planes can be expensive, so consider packing your snacks. This is one of the best travel hacks to save money even when you aren’t traveling. It’s also an easy way to ensure that you eat more healthily and stick to dietary programs.

10. Eat Out for Lunch Instead of Dinner

Looking for another money hack that actually works! Everyone needs to eat and if you’re lucky enough to find a hotel with breakfast included, don’t be afraid to grab a yogurt and fruit for mid-afternoon snacks. If you want to eat out, food is less expensive at lunchtime. Save a bit of your lunch, couple it with yogurt and fruit and you’ll have a light and nutritious dinner. 

11. Attend a Community Festival

While downtown Chicago has plenty of attractions, don’t forget to explore the city’s diverse neighborhoods. Each neighborhood has its unique character and attractions, and many are easily accessible via public transportation. Consider visiting popular Chicago neighborhoods like Wicker Park, Pilsen, Lakeview, Lincoln Park, Chinatown, and Greek Town.

  • June – The Taste of Chicago is an annual event held in Grant Park
  • July – Chicago Summer Dance (Grant Park)
  • August – The Chicago Air and Water Shop (along the Lake Front)
  • September – Taste of Greektown is a great opportunity to experience Grecian food and culture in Greektown. 

12. Explore Free Outdoor Markets

For those looking to explore all that Chicago has to offer while also saving some money, visiting the city’s many outdoor markets is a must.

Not only do they provide a unique way to get to know the city, but they also offer great deals on handmade crafts and souvenirs.

Here are three popular outdoor summer markets in Chicago that are worth a visit:

  • Green City Market: This weekly farmer’s market located in Lincoln Park features fresh produce from man local vendors, as well as cooking demonstrations and educational programs. As a bonus, there are plenty of food stalls offering delicious, affordable snacks. Chicago travel tip: Visit early for the best selection of fruits and vegetables.
  • Maxwell Street Market – Open on Sunday mornings, this famous open-air market features more than 400 stalls of vintage items, antiques, art, jewelry, and more. Prices tend to be quite reasonable, making it an ideal spot for bargain hunters. Chicago travel tip: Be sure to haggle for even better prices!
  • Randolph Street Market Festival – Held on the last weekend of every month, this outdoor market in the West Loop offers a vast array of antiques, collectibles, and unique finds from dozens of vendors. For those looking for great deals on vintage clothing and jewelry, this is the place to go. Chicago travel tip: Make sure to bring cash since some vendors do not accept cards.

13. Attend Free MUSIC Festivals

One of the best creative travel hacks in Chicago is attending free festivals.

With summer arriving soon, it will be the perfect time to explore some of Chicago’s most popular free music festivals. 

From outdoor concerts to block parties, there are plenty of opportunities to enjoy music without spending a lot of money.  

So, if you’re looking for something fun to do this summer, consider heading to one of these popular events!

  • June – Chicago hosts the largest free blues festival in the world, in Millennium Park. It features local and national blues musicians.
  • June through August – Grant Park Music Festival is an annual classical music event that features performances by the Grant Park Orchestra.
  • August – the Chicago Jazz Festival takes place every August. This free festival is held in Millennium Park and features several stages with various jazz acts performed throughout the day. 

14. Travel with a Friend or Group

Traveling with a friend or group is an easy way to save money on travel. When you share costs, such as lodging and transportation, with another person or a group, you can reduce the overall cost.

Additionally, if you have a larger group of people, you can take advantage of discounts offered for groups that many vendors offer. Sharing meals and entertainment activities also help to lower the costs of traveling together. 

As you can see, exploring Chicago doesn’t have to break the bank. You can visit new cities with friends or family can help make it more enjoyable and more economical. So make sure to consider these hacks on how to save money when traveling to Chicago during peak season.  

Final Thoughts on Travel Hacks to Save in Chicago

Whether you are visiting Chicago for the first time or returning to Rome because you tossed a coin into the Trevi fountain, these travel hacks will come in handy to make your stay enjoyable.

  • Be prepared! Read these tips on the essentials for an international flight.
  • Think comfort when flying coach, it will help you stay calm and confident.
  • Beware of scammers, pickpockets, and panhandlers. It’s a thing in Europe and it can happen when you least expect it. 

Here are a few more Chicago resources that may be of interest.

Safe travels!

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