Flights to Chicago, IL

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Traveling to Chicago, IL (MDW) (ORD)

Chicago, also called the Windy City, is the most happening city in the Midwest, with something to offer for every traveler. Take a spin on the Ferris wheel at Navy Pier, grab a slice of deep dish, check out Millennium Park and snap a photo with The Bean or take a tour on the river! Whether you are traveling with family or friends, there are a number of things to see and do when you are visiting Chicago.

Thinking about traveling to Chicago? Get to Chicago with ease by booking a flight into Chicago Midway International Airport (MDW) or Chicago O'Hare International Airport (ORD) on Frontier Airlines. Explore flight options and select one that suits your schedule, then start planning your trip!

Flying into Chicago? We also service Chicago O'Hare International Airport

Best Deals on Flights to Chicago, IL

$

Dallas, TX (DFW)To

Chicago, IL (ORD)
Departing Sep 9, 2026
From
$40
Last seen: 54 mins ago
One-way
Discount Den Basic Fare

Atlanta, GA (ATL)To

Chicago, IL (ORD)
Departing Sep 8, 2026
From
$33
Last seen: 10 hours ago
One-way
Discount Den Basic Fare

Atlanta, GA (ATL)To

Chicago, IL (MDW)
Departing Sep 1, 2026
From
$43
Last seen: 2 hours ago
One-way
Discount Den Basic Fare

Houston, TX (IAH)To

Chicago, IL (ORD)
Departing Sep 29, 2026
From
$47
Last seen: 6 hours ago
One-way
Discount Den Basic Fare

Orlando, FL (MCO)To

Chicago, IL (ORD)
Departing Sep 10, 2026
From
$41
Last seen: 1 hour ago
One-way
Discount Den Basic Fare

Denver, CO (DEN)To

Chicago, IL (ORD)
Departing Oct 3, 2026
From
$33
Last seen: 7 hours ago
One-way
Discount Den Basic Fare

Philadelphia, PA (PHL)To

Chicago, IL (ORD)
Departing Sep 7, 2026
From
$46
Last seen: 6 mins ago
One-way
Discount Den Basic Fare

Dallas, TX (DFW)To

Chicago, IL (MDW)
Departing Oct 13, 2026
From
$53
Last seen: 3 hours ago
One-way
Discount Den Basic Fare

Las Vegas, NV (LAS)To

Chicago, IL (ORD)
Departing Sep 22, 2026
From
$47
Last seen: 9 hours ago
One-way
Discount Den Basic Fare

Fort Lauderdale, FL (FLL)To

Chicago, IL (ORD)
Departing Oct 29, 2026
From
$22
Last seen: 10 hours ago
One-way
Discount Den Basic Fare

Los Angeles, CA (LAX)To

Chicago, IL (ORD)
Departing Sep 14, 2026
From
$53
Last seen: 6 hours ago
One-way
Discount Den Basic Fare

Baltimore, MD (BWI)To

Chicago, IL (ORD)
Departing Oct 31, 2026
From
$32
Last seen: 1 hour ago
One-way
Discount Den Basic Fare

Phoenix, AZ (PHX)To

Chicago, IL (ORD)
Departing Sep 15, 2026
From
$44
Last seen: 3 hours ago
One-way
Discount Den Basic Fare

San Juan, PR (SJU)To

Chicago, IL (ORD)
Departing Sep 17, 2026
From
$57
Last seen: 4 hours ago
One-way
Discount Den Basic Fare

Orlando, FL (MCO)To

Chicago, IL (MDW)
Departing Oct 7, 2026
From
$51
Last seen: 7 hours ago
One-way
Discount Den Basic Fare

Tampa, FL (TPA)To

Chicago, IL (ORD)
Departing Oct 22, 2026
From
$41
Last seen: 6 hours ago
One-way
Discount Den Basic Fare

Cancun, MX (CUN)To

Chicago, IL (ORD)
Departing Dec 5, 2026
From
$233
Last seen: 3 hours ago
One-way
Discount Den Basic Fare

Fort Myers, FL (RSW)To

Chicago, IL (ORD)
Departing Dec 7, 2026
From
$52
Last seen: 1 hour ago
One-way
Discount Den Basic Fare
*Prices found by others in the previous 48 hours for one-way flights. Prices shown may also require membership in our travel club, Discount Den®.

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Best Flight Deals to Chicago, IL with Frontier

$
Best Flight Deals to Chicago, IL with Frontier
From
To
Dallas, TX (DFW)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Sep 23, 2026

From

$40

Last seen: 6 hours ago

Atlanta, GA (ATL)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Oct 13, 2026

From

$33

Last seen: 5 hours ago

Atlanta, GA (ATL)Chicago, IL (MDW)One-way
/
Discount Den Basic Fare		Departing Sep 16, 2026

From

$43

Last seen: 1 hour ago

Houston, TX (IAH)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Sep 29, 2026

From

$47

Last seen: 6 hours ago

Orlando, FL (MCO)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Oct 29, 2026

From

$41

Last seen: 7 hours ago

Denver, CO (DEN)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Oct 3, 2026

From

$33

Last seen: 7 hours ago

Philadelphia, PA (PHL)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Nov 9, 2026

From

$46

Last seen: 4 hours ago

Dallas, TX (DFW)Chicago, IL (MDW)One-way
/
Discount Den Basic Fare		Departing Oct 13, 2026

From

$53

Last seen: 3 hours ago

Las Vegas, NV (LAS)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Sep 22, 2026

From

$47

Last seen: 9 hours ago

Fort Lauderdale, FL (FLL)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Oct 29, 2026

From

$22

Last seen: 10 hours ago

Los Angeles, CA (LAX)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Sep 14, 2026

From

$53

Last seen: 5 hours ago

Baltimore, MD (BWI)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Oct 31, 2026

From

$32

Last seen: 1 hour ago

Phoenix, AZ (PHX)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Sep 15, 2026

From

$44

Last seen: 3 hours ago

San Juan, PR (SJU)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Sep 17, 2026

From

$57

Last seen: 4 hours ago

Orlando, FL (MCO)Chicago, IL (MDW)One-way
/
Discount Den Basic Fare		Departing Oct 7, 2026

From

$51

Last seen: 7 hours ago

Tampa, FL (TPA)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Oct 22, 2026

From

$41

Last seen: 6 hours ago

Cancun, MX (CUN)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Dec 5, 2026

From

$233

Last seen: 3 hours ago

Fort Myers, FL (RSW)Chicago, IL (ORD)One-way
/
Discount Den Basic Fare		Departing Dec 7, 2026

From

$52

Last seen: 1 hour ago

*Prices found by others in the previous 48 hours for one-way flights. Prices shown may also require membership in our travel club, Discount Den®.
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