Heading to Chicago? The Windy City just might blow you away — and if you’re not careful, it’ll take your wallet too. If you’re looking for ways to cut costs while you travel, we have a few ideas.

Read on!

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Planning your trip

As a rule of thumb, Chicago is cheapest (and least crowded) during the offseason, but that’s also when the weather is notoriously cold. If you’d like to hit the sweet spot of affordable accommodation and comfortable temperatures, it’s best to visit the city during its shoulder season: during April, May, September, or October.

If the cold doesn’t bother you, you could also consider a trip in early or mid-December. You’ll enjoy the holiday festivities, but you won’t have to spend a small fortune on your hotel or deal with large throngs of tourists.

Airfare often drops in October and November as well — so keep an eye out for cheap flights. In general, you’ll get the best deal by booking your plane ticket to Chicago about two months in advance.

As always, hostels are a low-cost alternative to traditional hotels, and Chicago offers plenty of nice options. Try Hostelling International, Holiday Jones, or Freehand Chicago, all comfortable establishments that offer dorm beds at low prices.

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Seeing the sights

Thanks to discount tickets, free attractions, and walking tours, exploring Chicago doesn’t have to be expensive.

Many travelers save by purchasing a City Pass, which includes admission to five major Chicago sights for $106. The pass is valid for nine days after its first use, so you’ll have more than enough time to see the city. Alternatively, Smart Destinations will let you customize a sightseeing pass by bundling two or more attractions onto one ticket, resulting in savings of 20 to 25 percent.

Of course, several Chicago hotspots are free of charge, including Millennium Park (home to the city’s famous Cloud Gate, often called “the Bean”). What’s more, the Lincoln Park Zoo doesn’t charge admission, and Navy Pier is free, although the pier’s restaurants and rides are not.

At most Chicago museums, only Illinois residents are eligible for free admission (and only on certain days), so visitors will not benefit from such programs. That said, most museums do offer discounted student admission — so, if you’re in college, remember to take your student ID on your trip. Or, if your itinerary includes the Art Institute, the Field Museum, the Museum of Science and Industry, Shedd Aquarium, or Adler Planetarium, you should strongly consider purchasing a sightseeing pass.

As an alternative to visiting the city’s major museums, you could tour the free Chicago Cultural Center, which is home to the largest Tiffany stained-glass dome in the world, or the National Museum of Mexican Art. Another thing to note is that the Museum of Contemporary Art and the Oriental Institute Museum have suggested-admission policies — so pay what you can, but don’t be too cheap!

Another great way to get to know the city is by asking a local to show you around. Chicago Greeter lets guests customize free tours based on language, interests, and neighborhoods of choice, so you’ll have the freedom to plan your own excursion. Just make sure that you reserve your tour at least 10 business days in advance.

Checking out the view

Two of the city’s most famous (and expensive) attractions are the Skydeck and 360 Chicago, both of which offer stunning views from more than 1,000 feet in the air. However, if you haven’t picked up a sightseeing pass, visiting these viewpoints might push your budget to its breaking point.

Luckily, there are a few other ways to enjoy spectacular views around the Windy City. Head to a rooftop bar — like LH Rooftop, Cerise, or Streeterville Social — and check out the view while you sip on a drink. (You might want to look up the cocktail menu before you go, though, as some of the rooftop bars only offer pricey drinks.)

For a quieter look at Chicago’s skyline, you could go to the Intercontinental Hotel, located on the Magnificent Mile, and take the elevator to the top of the Executive Tower. There, you’ll have an excellent view of the Tribune Tower and other nearby buildings.

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Chowing down

Even people on extremely tight budgets can eat well in Chicago. And, of course, you can’t leave the city without trying a classic deep-dish pizza — so head to Pequod’s Pizza, Pizano’s, or Giordano’s for delicious, reasonably priced offerings of Chicago’s most famous entrée.

Once you cross that off your list, you can move on to some of the city’s other options. Try a hot dog at Superdawg or Gene and Jude’s, or go to Taqueria El Asadero for steak tacos. And, if you’d like to eat at Illinois’s favorite fast-food chain, Portillo’s is the place to go, as they happily serve up tasty fare and their iconic cake shakes.

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Getting around

Whether you’re traveling on a budget or not, renting a car is a bad idea in the Windy City. Parking spaces are extremely hard to come by, and garages charge an exorbitant amount. Similarly, taxis and ride-sharing services are fairly expensive.

That said, Chicago’s well-connected public transportation system offers an excellent way to get around the city. It costs $5 to purchase a Ventra transit card, but the fee is waived for customers who order online, and the five-dollar amount is refunded to anyone who registers the card online within 90 days of purchase.

A one-day pass costs $10, a three-day pass $20, and a weekly pass $28. With your Ventra card, you can take an unlimited number of train and bus rides, making public transportation a cost-efficient way to travel across Chicago.

If you’d like to get some exercise while exploring the city, then you might want to ride a Divvy bike. With 580 stations and 5,800 bikes scattered around Chicagoland, renting is both convenient and affordable — just pay $3 for a single ride or $15 for a day pass, then leave your bike at any station when you’re done.

Ready to get going? We’ll see you in the Windy City!

Cover photo by Sawyer Bengtson

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Whitney Brown
Whitney Brown is a recent journalism graduate and travel writer based in Utah. She has lived in France and Ireland, and she's always planning her next big adventure. In addition to her passion for travel, Whitney loves archaeology, photography and floral design.