$32 Cheap Flights to Chicago, IL

View $38 flight on Wed, Jun 4, 2025Opens in a new window

Popular airlines to Chicago

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Find available prices by choosing your travel dates.

How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at $32 for one-way flights and $64 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, May 31 - Tue, Jun 3
EWR
New York
ORD
Chicago
$77 Roundtrip, just found
$77
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 31 from New York to Chicago, returning Tue, Jun 3, priced at $77 just found
American Airlines
Sat, May 24 - Wed, May 28
EWR
New York
ORD
Chicago
$107 Roundtrip, just found
$107
Roundtrip
just found
Select American Airlines flight, departing Sat, May 24 from New York to Chicago, returning Wed, May 28, priced at $107 just found
United
Tue, May 27 - Tue, Jun 3
EWR
New York
ORD
Chicago
$115 Roundtrip, just found
$115
Roundtrip
just found
Select United flight, departing Tue, May 27 from New York to Chicago, returning Tue, Jun 3, priced at $115 just found
Frontier Airlines
Fri, May 23 - Sun, May 25
LAX
Los Angeles
ORD
Chicago
$130 Roundtrip, just found
$130
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 23 from Los Angeles to Chicago, returning Sun, May 25, priced at $130 just found
Delta
Sun, May 25 - Wed, May 28
LGA
New York
ORD
Chicago
$137 Roundtrip, found 6 hours ago
$137
Roundtrip
found 6 hours ago
Select Delta flight, departing Sun, May 25 from New York to Chicago, returning Wed, May 28, priced at $137 found 6 hours ago

Frequently asked questions

What month is the cheapest to fly to Chicago?
May is typically the least expensive month for flights to Chicago*. Check for affordable fares during this time as you could score a good deal. *Cheapest month to fly is based on the month with the cheapest flight found on Expedia.com in the next 330 days.
Which US cities have the cheapest flights to Chicago?
New York, Washington and Dallas generally offer cheap flights to Chicago. Remember that fares vary based on factors such as holiday periods, number of stopovers and demand.
Which US cities fly direct to Chicago?
You can fly to Chicago directly from 150 US cities. To find a nonstop journey, check “Direct flights only” when browsing for flights to Chicago on Expedia. Then, compare the options and pick the best departure from any of these cities:

  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix

How to find a cheap flight to Chicago?
Book in advance or look for cheap flights to Chicago during off-season months like December and January. Leaving on a Thursday can also save you 16% on average compared to a Sunday flight.* The Expedia app makes it even easier to know exactly when to book. Just turn on the toggle for “Watch prices” and you’ll get notified when there’s a better deal.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation’s (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Chicago?
Although booking in advance is typically the best way to save cash, don’t worry if your Chicago getaway is last minute. You can still find cheap flights to Chicago, especially if your plans have some flexibility. Try switching up your travel dates, exploring different ticket options or flying out of another hub.
How far in advance should I book a flight to Chicago?
Secure your flight to Chicago two to four months ahead if you’re visiting from an international destination. For domestic travel, the timeframe is around 28 days in advance. Bigger savings and a greater choice of departure dates, times and seating options are some of the great reasons to book early.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation’s (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Chicago?
Sundays are usually the best day to book a cheap flight to Chicago, with savings of around 8% on average compared to Fridays. If you purchase tickets on a Friday, be ready to pay a higher price as this is often the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation’s (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Chicago?
Chicago has connections to 216 airports globally through 44 airlines, with O’Hare Intl. Airport (ORD) as its primary entry point. Pick from these top airlines to Chicago when planning your journey:

  • United Airlines
  • American Airlines
  • Delta Air Lines
  • Alaska Airlines

Where do you fly into Chicago?
The main hub when you fly to Chicago is Midway Intl. Airport (MDW), but there are other nearby options like O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT). You can also arrive at Gary, IN (GYY-Gary - Chicago Intl.) and Chicago Executive Airport (PWK) when flying to Chicago.
How far is the airport from central Chicago?
Jetting into Midway Intl. Airport (MDW) puts you around 9 mi southwest of the center of Chicago.
Can I save money by booking a Chicago trip package?
Bundle your flights and accommodations and you could save hundreds of dollars. What’s more, you can add extras like tours and car rentals to your Chicago flight and hotel package deal. With Expedia, it’s simple to organize all your Chicago travel arrangements in the same place.
Can I change or cancel my flight to Chicago?
If you bought your flight to Chicago within the last 24 hours, you can usually change or cancel it for free. After that, extra charges may apply depending on the airline’s rules and restrictions. For more information, check out our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be offered a credit for future flights instead of a direct refund. When browsing on Expedia, select the “Changes included” or “No cancel fee” filters to see tickets with flexible change policies.

Trending flights to Chicago

Prices were available within the past 7 days and start at $32 for one-way flights and $64 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Mon, May 12 - Thu, May 15
ATL
Atlanta
ORD
Chicago
$64 Roundtrip, just found
$64
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, May 12 from Atlanta to Chicago, returning Thu, May 15, priced at $64 just found
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