$29 Cheap Flights to Chicago, IL

View $29 flight on Sat, May 2, 2026Opens in a new window

Popular airlines to Chicago

How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at $29 for one-way flights and $68 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Apr 29 - Tue, May 5
LAX
Los Angeles
ORD
Chicago
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Apr 29 from Los Angeles to Chicago, returning Tue, May 5, priced at $68 just found
Spirit Airlines
Fri, Apr 24 - Tue, Apr 28
ATL
Atlanta
ORD
Chicago
$73 Roundtrip, just found
$73
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Apr 24 from Atlanta to Chicago, returning Tue, Apr 28, priced at $73 just found
United
Tue, May 12 - Wed, May 13
EWR
New York
ORD
Chicago
$155 Roundtrip, just found
$155
Roundtrip
just found
Select United flight, departing Tue, May 12 from New York to Chicago, returning Wed, May 13, priced at $155 just found
American Airlines
Sat, Jul 18 - Mon, Jul 20
EWR
New York
ORD
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select American Airlines flight, departing Sat, Jul 18 from New York to Chicago, returning Mon, Jul 20, priced at $177 just found
Southwest Airlines
Wed, Jun 3 - Tue, Jun 9
ATL
Atlanta
MDW
Chicago
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Jun 3 from Atlanta to Chicago, returning Tue, Jun 9, priced at $197 just found

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $346
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $346
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $439
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $439

Frequently asked questions

What month is the cheapest to fly to Chicago?
The cheapest month to fly to Chicago is April when demand is low. Off-peak months are typically when you'll find cheap flights. To keep costs down, steer clear of flying during school breaks and major holidays.
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.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$68

Trending flights to Chicago

Prices were available within the past 7 days and start at $29 for one-way flights and $68 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Apr 29 - Tue, May 5
LAX
Los Angeles
ORD
Chicago
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Apr 29 from Los Angeles to Chicago, returning Tue, May 5, priced at $68 just found

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