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Flight Deals to Chicago from $53

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Bundle + Save

Top flight deals from leading airlines:

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... and +100s more

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Save an average of $240 per person when bundling your flight and hotel together with Priceline

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Stops

  • Nonstop
    from $178
  • Up to 1 stop
    $125
  • Up to 2 stops
    $439

Airlines

  • American Airlines
    $238
  • Delta Air Lines
    $178
  • Frontier Airlines
    $171
  • Hawaiian Airlines
    $582
  • Spirit Airlines
    $125
  • United Airlines
    $238

Cabin Class

  • Economy
    $125

Departure Airports

  • Detroit Metropolitan Airport
    $125

Arrival Airports

  • Chicago Midway Airport
    $171
  • Chicago O Hare Airport
    $125

Layover Airports

  • Baltimore/Washington International Thurgood Marshall Airport
    $159
  • Charlotte Douglas International Airport
    $274
  • Dallas Fort Worth International Airport
    $297
  • Denver International Airport
    $570
  • General Edward Lawrence Logan International Airport
    $439
  • George Bush Intercontinental Houston Airport
    $125
  • Hartsfield Jackson Atlanta International Airport
    $171
  • Louis Armstrong New Orleans International Airport
    $184
  • Myrtle Beach International Airport
    $125
  • Nashville International Airport
    $1052
  • New York LaGuardia Airport
    $439
  • Newark Liberty Airport
    $337
  • Orlando International Airport
    $159
  • Philadelphia International Airport
    $531
  • Raleigh Durham International Airport
    $211
  • Reagan Washington National Airport
    $417
  • Seattle Tacoma International Airport
    $582
  • Tampa International Airport
    $159
  • Washington Dulles Airport
    $343

Best Price. GUARANTEED.

Exclusively for Priceline Members
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On average save $240 per traveler
Spirit Airlines Logo
Spirit Airlines

05/20/25

DTW
8h
IAH

05/20/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/24/25

ORD
6h 2m
MYR

05/24/25

DTW
$125
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/22/25

DTW
3h 42m
BWI

05/22/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/29/25

ORD
9h 4m
MCO

05/29/25

DTW
$159
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/09/25

DTW
10h 21m
TPA

06/09/25

ORD
Spirit Airlines Logo
Spirit Airlines

06/16/25

ORD
8h 45m
MYR

06/16/25

DTW
$159
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/28/25

DTW
6h 10m
ATL

05/28/25

MDW
Frontier Airlines Logo
Frontier Airlines

06/04/25

MDW
8h 34m
ATL

06/04/25

DTW
$171
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/24/25

DTW
15m
Direct

05/24/25

MDW
Delta Air Lines Logo
Delta Air Lines

05/25/25

MDW
2h 19m
Direct

05/25/25

DTW
$178
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/25/25

DTW
15m
Direct

05/25/25

MDW
Delta Air Lines Logo
Delta Air Lines

05/31/25

MDW
2h 25m
Direct

05/31/25

DTW
$178
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/06/25

DTW
8h 13m
MSY

06/06/25

ORD
Spirit Airlines Logo
Spirit Airlines

06/08/25

ORD
9h 43m
TPA

06/08/25

DTW
$184
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/22/25

DTW
6h 12m
ATL

05/23/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/29/25

ORD
9h 32m
RDU

05/29/25

DTW
$211
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/25/25

DTW
31m
Direct

05/25/25

ORD
United Airlines Logo
United Airlines

05/31/25

ORD
2h 34m
Direct

05/31/25

DTW
$238
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/24/25

DTW
40m
Direct

05/24/25

ORD
American Airlines Logo
American Airlines

05/25/25

ORD
2h 32m
Direct

05/25/25

DTW
$238
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

DTW
30m
Direct

05/24/25

ORD
United Airlines Logo
United Airlines

05/31/25

ORD
2h 32m
Direct

05/31/25

DTW
$238
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/20/25

DTW
6h 8m
CLT

05/20/25

ORD
American Airlines Logo
American Airlines

05/24/25

ORD
2h 23m
Direct

05/24/25

DTW
$274
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/24/25

DTW
5h 19m
CLT

05/24/25

ORD
American Airlines Logo
American Airlines

05/25/25

ORD
2h 32m
Direct

05/25/25

DTW
$274
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

DTW
28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/11/25

ORD
6h 39m
CLT

06/11/25

DTW
$274
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/02/25

DTW
40m
Direct

06/02/25

ORD
American Airlines Logo
American Airlines

06/04/25

ORD
9h 59m
DFW

06/04/25

DTW
$297
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/03/25

DTW
7h 32m
EWR

06/03/25

ORD
United Airlines Logo
United Airlines

06/10/25

ORD
2h 34m
Direct

06/10/25

DTW
$337
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/07/25

DTW
12h 17m
IAD

06/08/25

ORD
United Airlines Logo
United Airlines

06/08/25

ORD
2h 32m
Direct

06/08/25

DTW
$343
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/14/25

DTW
6h 18m
CLT

05/14/25

ORD
American Airlines Logo
American Airlines

05/28/25

ORD
12h 56m
DCA

05/29/25

DTW
$417
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/02/25

DTW
6h 18m
CLT

06/02/25

ORD
American Airlines Logo
American Airlines

06/04/25

ORD
9h 56m
BOS
LGA

06/04/25

DTW
$439
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/07/25

DTW
6h 55m
DFW

06/07/25

ORD
American Airlines Logo
American Airlines

06/08/25

ORD
10h 22m
PHL

06/08/25

DTW
$531
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/18/25

DTW
12h 47m
DEN

05/18/25

ORD
United Airlines Logo
United Airlines

05/25/25

ORD
15h 4m
IAD

05/25/25

DTW
$570
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/31/25

DTW
11h 55m
SEA

05/31/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

06/02/25

ORD
11h 16m
SEA

06/03/25

DTW
$582
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

06/03/25

DTW
11h 55m
SEA

06/03/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

06/09/25

ORD
11h 16m
SEA

06/10/25

DTW
$582
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/07/25

DTW
3h 45m
IAD

06/07/25

ORD
United Airlines Logo
United Airlines

06/08/25

ORD
5h 33m
BNA

06/08/25

DTW
$1052
Free cancellation within 83 hours of booking

Top Deals on flights to Chicago

Denver, US (DEN) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jun 24

DEN
3h 38m
Direct

Jun 24

ORD

as low as

$53

Denver, US (DEN) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Aug 14

DEN
3h 28m
Direct

Aug 14

MDW

as low as

$57

Denver, US (DEN) - Chicago, US (CHI)

 Logo

Jun 24

DEN
3h 38m
Direct

Jun 24

ORD

as low as

$58

Denver, US (DEN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 18

DEN
3h 40m
Direct

Jun 18

ORD

as low as

$75

Denver, US (DEN) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 14

DEN
9h 37m
ATL

May 14

ORD

as low as

$97

Denver, US (DEN) - Chicago, US (CHI)

 Logo

Jun 9

DEN
3h 35m
Direct

Jun 9

ORD

as low as

$102

Denver, US (DEN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 1

DEN
6h 49m
DFW

Jul 1

ORD

as low as

$104

Denver, US (DEN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 24

DEN
7h 57m
CLT

Jun 24

ORD

as low as

$104

Denver, US (DEN) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 25

DEN
3h 35m
Direct

Jun 26

ORD

as low as

$105

Denver, US (DEN) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 4

DEN
5h 13m
MSP

Jun 4

ORD

as low as

$108

Denver, US (DEN) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 29

DEN
7h 44m
DTW

Jul 29

MDW

as low as

$108

Denver, US (DEN) - Chicago, US (CHI)

 Logo

May 24

DEN
5h 53m
MSP

May 24

ORD

as low as

$108
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