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Flight Deals from New York City to Chicago Midway Airport from $84

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Bundle + Save

Top flight deals from leading airlines:

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... and +100s more

Incredible Deals

Save up to 50% on select flights with Priceline

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

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Price Drop Deals Near You

Chicago

28% Price Drop

Jul 12

EWR

4 days

Jul 16

MDW

$257

now only

$184

Rond Trip

Stops

  • Up to 1 stop
    $142
  • Up to 2 stops
    $725

Airlines

  • Delta Air Lines
    $142
  • Frontier Airlines
    $313
  • United Airlines
    $725

Cabin Class

  • Economy
    $142

Departure Airports

  • New York John F Kennedy Airport
    $227
  • New York LaGuardia Airport
    $313
  • Newark Liberty Airport
    $142

Arrival Airports

  • Chicago Midway Airport
    $142

Layover Airports

  • Denver International Airport
    $960
  • Detroit Metropolitan Airport
    $142
  • Hartsfield Jackson Atlanta International Airport
    $176
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $151
  • Orlando International Airport
    $333
  • Raleigh Durham International Airport
    $1120
  • Washington Dulles Airport
    $725

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

BUNDLE & SAVE

Book a flight & hotel together for extra savings.

On average save $240 per traveler
Delta Air Lines Logo
Delta Air Lines

09/17/25

EWR
2h 52m
DTW

09/17/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/23/25

MDW
3h 17m
Direct

09/23/25

EWR
$142
Delta Air Lines Logo
Delta Air Lines

08/30/25

EWR
5h 10m
MSP

08/30/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/03/25

MDW
3h 15m
Direct

09/03/25

EWR
$151
Delta Air Lines Logo
Delta Air Lines

09/17/25

EWR
2h 52m
DTW

09/17/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/23/25

MDW
6h 28m
DTW

09/23/25

EWR
$156
Delta Air Lines Logo
Delta Air Lines

09/12/25

EWR
6h 7m
MSP

09/12/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/27/25

MDW
3h 18m
Direct

09/27/25

EWR
$162
Delta Air Lines Logo
Delta Air Lines

09/12/25

EWR
6h 7m
MSP

09/12/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/24/25

MDW
5h 53m
DTW

09/24/25

EWR
$176
Delta Air Lines Logo
Delta Air Lines

08/30/25

EWR
5h 10m
MSP

08/30/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/03/25

MDW
4h 48m
DTW

09/03/25

EWR
$176
Delta Air Lines Logo
Delta Air Lines

09/10/25

EWR
2h 38m
DTW

09/10/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/20/25

MDW
6h 58m
ATL

09/21/25

EWR
$176
Delta Air Lines Logo
Delta Air Lines

09/03/25

EWR
2h 38m
DTW

09/03/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/13/25

MDW
6h 16m
MSP

09/13/25

EWR
$176
Delta Air Lines Logo
Delta Air Lines

09/06/25

EWR
2h 38m
DTW

09/06/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/27/25

MDW
7h 16m
ATL

09/27/25

EWR
$176
Delta Air Lines Logo
Delta Air Lines

09/16/25

EWR
4h 55m
ATL

09/16/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/19/25

MDW
6h 20m
ATL

09/19/25

EWR
$186
Delta Air Lines Logo
Delta Air Lines

09/25/25

EWR
5h 58m
ATL

09/25/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/29/25

MDW
3h 20m
Direct

09/29/25

EWR
$189
Delta Air Lines Logo
Delta Air Lines

09/25/25

EWR
5h 58m
ATL

09/25/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/29/25

MDW
6h 23m
DTW

09/29/25

EWR
$223
Delta Air Lines Logo
Delta Air Lines

09/18/25

JFK
5h 37m
DTW

09/18/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/23/25

MDW
5h 18m
DTW

09/23/25

JFK
$227
Delta Air Lines Logo
Delta Air Lines

09/14/25

JFK
5h 8m
ATL

09/14/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/20/25

MDW
6h 16m
MSP

09/20/25

JFK
$257
Frontier Airlines Logo
Frontier Airlines

09/03/25

LGA
7h 31m
ATL

09/03/25

MDW
Frontier Airlines Logo
Frontier Airlines

09/07/25

MDW
6h 49m
ATL

09/07/25

LGA
$313
Frontier Airlines Logo
Frontier Airlines

09/12/25

LGA
6h 48m
ATL

09/12/25

MDW
Frontier Airlines Logo
Frontier Airlines

09/15/25

MDW
6h 49m
ATL

09/15/25

LGA
$317
Frontier Airlines Logo
Frontier Airlines

09/05/25

JFK
5h 17m
ATL

09/05/25

MDW
Frontier Airlines Logo
Frontier Airlines

09/06/25

MDW
6h 55m
ATL

09/07/25

JFK
$317
Frontier Airlines Logo
Frontier Airlines

09/01/25

JFK
8h 30m
MCO

09/01/25

MDW
Frontier Airlines Logo
Frontier Airlines

09/03/25

MDW
8h 40m
ATL

09/03/25

JFK
$333
United Airlines Logo
United Airlines

09/21/25

EWR
4h 14m
ATL

09/21/25

MDW
United Airlines Logo
United Airlines

09/24/25

MDW
9h 10m
DTW
IAD

09/24/25

EWR
$725
United Airlines Logo
United Airlines

09/18/25

EWR
4h 14m
ATL

09/18/25

MDW
United Airlines Logo
United Airlines

09/25/25

MDW
12h 50m
DEN
IAD

09/25/25

EWR
$960
Delta Air Lines Logo
Delta Air Lines

09/08/25

EWR
11h 54m
RDU
ATL

09/08/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/12/25

MDW
5h 51m
DTW

09/12/25

EWR
$1120
Delta Air Lines Logo
Delta Air Lines

09/08/25

EWR
11h 54m
RDU
ATL

09/08/25

MDW
Delta Air Lines Logo
Delta Air Lines

09/12/25

MDW
7h 52m
ATL
RDU

09/12/25

EWR
$1815

Top Deals on flights from New York City to Chicago Midway Airport

New York City, US (NYC) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jul 16

EWR
4h 41m
ATL

Jul 16

MDW

as low as

$84

New York City, US (NYC) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jul 8

EWR
4h 41m
ATL

Jul 8

MDW

as low as

$84

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 9

EWR
5h 25m
DTW

Jul 9

MDW

as low as

$98

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 22

EWR
5h 58m
ATL

Jul 22

MDW

as low as

$98

New York City, US (NYC) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jul 14

JFK
8h 7m
MCO

Jul 14

MDW

as low as

$104

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 10

EWR
6h 46m
MSP

Jul 10

MDW

as low as

$148

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 7

EWR
2h 44m
DTW

Jul 7

MDW

as low as

$148

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 4

LGA
11h 16m
DCA
DTW

Jul 5

MDW

as low as

$158

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 1

JFK
7h 11m
ATL

Jul 1

MDW

as low as

$164

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 30

LGA
11h 16m
DCA
DTW

Jul 1

MDW

as low as

$167

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jul 24

EWR
5h 13m
MSP

Jul 24

MDW

as low as

$178

New York City, US (NYC) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jul 21

JFK
8h 7m
MCO

Jul 21

MDW

as low as

$223