$27 Cheap Flights to Chicago, IL

View $27 flight on Wed, May 28, 2025Opens in a new window

How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at $27 for one-way flights and $74 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Fri, May 16 - Mon, May 19
ATL
Atlanta
ORD
Chicago
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 16 from Atlanta to Chicago, returning Mon, May 19, priced at $74 just found
Spirit Airlines
Wed, May 28 - Tue, Jun 3
LGA
New York
ORD
Chicago
$77 Roundtrip, found 2 hours ago
$77
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, May 28 from New York to Chicago, returning Tue, Jun 3, priced at $77 found 2 hours ago
Frontier Airlines
Tue, Jun 3 - Tue, Jun 17
ATL
Atlanta
MDW
Chicago
$82 Roundtrip, found 5 days ago
$82
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jun 3 from Atlanta to Chicago, returning Tue, Jun 17, priced at $82 found 5 days ago
Frontier Airlines
Tue, Jun 17 - Tue, Jun 17
DFW
Dallas
MDW
Chicago
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 17 from Dallas to Chicago, returning Tue, Jun 17, priced at $101 found 1 day ago
Frontier Airlines
Tue, Jun 3 - Tue, Jun 3
DFW
Dallas
ORD
Chicago
$107 Roundtrip, found 7 hours ago
$107
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Jun 3 from Dallas to Chicago, returning Tue, Jun 3, priced at $107 found 7 hours ago

Chicago Flights

Chicago Airports

When youíre looking to book flights to Chicago, Illinois, there are two airports that serve the Windy City. O'Hare International Airport is the main one, while Chicago Midway International Airport is considered the secondary tarmac.

O'Hare sits 17 miles northwest of the Loop. It provides plenty of amenities to keep you entertained while you wait for your flight or transportation into Chi-Town. If youíre hungry, youíre in luck. This airport boasts a variety of restaurants and cafes, providing sit-down cuisine and meals-on-the-go. The airport also features various shops, where you can find Chicago souvenirs, designer goods, electronics, and duty-free products. To top it all off, O'Hare provides spa services and even a yoga room to help keep you relaxed and rejuvenated during your travels.

Located roughly 12 miles northwest of downtown Chicago, Midway Airport includes several shops, the majority of which are located in the Midway Boulevard. You can also find restaurants, snack shops, and fast-food options when youíre looking fuel up before or after your flight. While youíre traveling through the airport, look for the public art and installation collections throughout the terminal.

Airport Transportation

When you have Chicago flights, rest assured knowing that both airports provide ground transportation. Here at Expedia.com, you can reserve Chicago car rentals and pick up your vehicle at your preferred airport. Alternatively, you can take advantage of public transportation as the Chicago Transit Authority provides both train and bus service to Midway and OíHare. Other transportation options include taxis, shuttles, and limousines.

Chicago Activities

Once youíve decided itís time to book plane tickets to Chicago, IL, start planning your adventures. The Windy City is home to fascinating exhibits, from the galleries at the Museum of Contemporary Art to the artifacts at the Chicago History Museum. For some of the best views of the skyline, venture up to the 360 Chicago observatory deck in the John Hancock building or the Skydeck Chicago in the Willis Tower. While youíre in town, chow down on some famous deep-dish pizza or Chicago-style hot dogs for an authentic taste of the city. Then round out your day with reservations at one of the best hotels in Chicago.

Planning Your Trip

The best times to visit Chicago are between April and May and September and October. Temperatures are moderate during these months, and the high season hasnít hit yet. Summertime is considered the most popular time to visit, so you may face more crowds and more expensive rates during this season. Meanwhile, winter brings temperatures in the low 30s F and a high chance of snowstorms.

Regardless of when you plan to visit, Expedia.com is here to match you with cheap flights to Chicago. Sort through our selection to find discounts on round-trip tickets that suit your price range. You can even use our mobile booking app for convenient access to exclusive online deals on airfare to Chicago. Book your affordable flights right here and start getting a taste for that delicious deep-dish pizza.

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.
Flights to Chicago information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$74

Trending flights to Chicago

Prices were available within the past 7 days and start at $27 for one-way flights and $74 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Fri, May 16 - Mon, May 19
ATL
Atlanta
ORD
Chicago
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 16 from Atlanta to Chicago, returning Mon, May 19, priced at $74 just found

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