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Incredible Deals
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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
Stops
- Nonstopfrom $392
- Up to 1 stop$185
- Up to 2 stops$356
Airlines
- Delta Air Lines$196
- Frontier Airlines$185
- Southwest Airlines$392
- United Airlines$521
Cabin Class
- Economy$185
Departure Airports
- New York John F Kennedy Airport$235
- New York LaGuardia Airport$212
- Newark Liberty Airport$185
Arrival Airports
- Chicago Midway Airport$185
Layover Airports
- Cincinnati Northern Kentucky International Airport$838
- Dallas Love Field$420
- Detroit Metropolitan Airport$196
- Hartsfield Jackson Atlanta International Airport$185
- Orlando International Airport$244
- Reagan Washington National Airport$356
- Washington Dulles Airport$800
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
06/18/25
EWR
4h 42m
ATL
06/18/25
MDW
06/18/25
MDW
7h 6m
ATL
06/19/25
EWR
$185
06/17/25
EWR
4h 42m
ATL
06/17/25
MDW
06/18/25
MDW
7h 6m
ATL
06/19/25
EWR
$185
06/11/25
EWR
6h 56m
ATL
06/11/25
MDW
06/18/25
MDW
7h 6m
ATL
06/19/25
EWR
$185
07/08/25
EWR
4h 41m
ATL
07/08/25
MDW
07/15/25
MDW
7h 6m
ATL
07/16/25
EWR
$189
07/09/25
EWR
4h 41m
ATL
07/09/25
MDW
07/15/25
MDW
7h 6m
ATL
07/16/25
EWR
$189
06/18/25
EWR
2h 41m
DTW
06/18/25
MDW
06/28/25
MDW
4h 40m
DTW
06/28/25
EWR
$196
06/17/25
EWR
2h 41m
DTW
06/17/25
MDW
06/21/25
MDW
5h 7m
DTW
06/21/25
EWR
$196
06/10/25
EWR
5h 25m
ATL
06/10/25
MDW
06/24/25
MDW
7h 6m
ATL
06/25/25
EWR
$197
06/12/25
LGA
7h 19m
ATL
06/12/25
MDW
06/17/25
MDW
7h 6m
ATL
06/18/25
LGA
$212
06/16/25
EWR
6h 16m
ATL
06/16/25
MDW
06/30/25
MDW
3h 13m
Direct
06/30/25
EWR
$216
06/16/25
EWR
6h 16m
ATL
06/16/25
MDW
06/30/25
MDW
5h 30m
DTW
06/30/25
EWR
$231
06/15/25
LGA
7h 19m
ATL
06/15/25
MDW
06/24/25
MDW
7h 6m
ATL
06/25/25
LGA
$234
06/15/25
EWR
6h
ATL
06/15/25
MDW
06/30/25
MDW
3h 13m
Direct
06/30/25
EWR
$235
06/10/25
EWR
5h 40m
DTW
06/10/25
MDW
06/17/25
MDW
3h 13m
Direct
06/17/25
EWR
$235
06/21/25
JFK
7h 11m
ATL
06/21/25
MDW
06/25/25
MDW
6h 59m
DTW
06/25/25
JFK
$235
06/10/25
JFK
5h 42m
DTW
06/10/25
MDW
06/17/25
MDW
7h 20m
ATL
06/17/25
JFK
$240
06/16/25
JFK
13h 18m
MCO
06/16/25
MDW
06/19/25
MDW
8h 31m
ATL
06/19/25
JFK
$244
06/29/25
LGA
7h 19m
ATL
06/29/25
MDW
07/02/25
MDW
7h 6m
ATL
07/03/25
LGA
$269
06/30/25
LGA
18h 16m
DCA
ATL
07/01/25
MDW
07/03/25
MDW
12h 50m
DTW
DCA
07/04/25
LGA
$356
06/24/25
EWR
13h 41m
ATL
DTW
06/25/25
MDW
06/30/25
MDW
4h 57m
DTW
06/30/25
EWR
$375
06/19/25
LGA
1h 25m
Direct
06/19/25
MDW
06/22/25
MDW
3h 5m
Direct
06/22/25
LGA
$392
06/30/25
JFK
14h 44m
DCA
DTW
07/01/25
MDW
07/03/25
MDW
5h 20m
DTW
07/03/25
JFK
$395
06/19/25
LGA
1h 25m
Direct
06/19/25
MDW
06/22/25
MDW
10h 10m
DAL
06/22/25
LGA
$420
07/03/25
EWR
25h
ATL
DTW
07/04/25
MDW
07/10/25
MDW
8h 24m
ATL
07/10/25
EWR
$495
06/26/25
EWR
2h 41m
DTW
06/26/25
MDW
07/06/25
MDW
3h 18m
Direct
07/06/25
EWR
$521
06/16/25
EWR
6h 16m
ATL
06/16/25
MDW
06/30/25
MDW
9h 50m
DTW
DCA
06/30/25
EWR
$645
06/25/25
EWR
2h 41m
DTW
06/25/25
MDW
06/25/25
MDW
9h 16m
ATL
DCA
06/25/25
EWR
$656
06/15/25
EWR
6h
ATL
06/15/25
MDW
06/24/25
MDW
9h 50m
DTW
DCA
06/24/25
EWR
$659
06/24/25
EWR
6h 29m
IAD
DTW
06/24/25
MDW
06/29/25
MDW
4h 57m
DTW
06/29/25
EWR
$800
07/09/25
LGA
11h 12m
CVG
ATL
07/09/25
MDW
07/15/25
MDW
8h 21m
ATL
CVG
07/15/25
LGA
$838
Top Deals on flights from New York City to Chicago Midway Airport
New York City, US (NYC) - Chicago, US (CHI)
Jul 1
LGA
1h 25m
Direct
Jul 1
MDW
as low as
$72
New York City, US (NYC) - Chicago, US (CHI)
Jul 15
EWR
5h 13m
MSP
Jul 15
MDW
as low as
$98
New York City, US (NYC) - Chicago, US (CHI)
Jul 12
EWR
2h 44m
DTW
Jul 12
MDW
as low as
$98
New York City, US (NYC) - Chicago, US (CHI)
Jul 9
EWR
2h 44m
DTW
Jul 9
MDW
as low as
$98
New York City, US (NYC) - Chicago, US (CHI)
Jul 9
EWR
4h 41m
ATL
Jul 9
MDW
as low as
$104
New York City, US (NYC) - Chicago, US (CHI)
Jun 25
EWR
4h 42m
ATL
Jun 25
MDW
as low as
$104
New York City, US (NYC) - Chicago, US (CHI)
Jul 14
JFK
5h 40m
DTW
Jul 14
MDW
as low as
$148
New York City, US (NYC) - Chicago, US (CHI)
Jun 29
LGA
7h 19m
ATL
Jun 29
MDW
as low as
$154
New York City, US (NYC) - Chicago, US (CHI)
Jul 3
LGA
26h 41m
DCA
DTW
Jul 4
MDW
as low as
$158
New York City, US (NYC) - Chicago, US (CHI)
Jun 22
JFK
31h 57m
LAS
Jun 23
MDW
as low as
$161
New York City, US (NYC) - Chicago, US (CHI)
Jul 18
LGA
11h 19m
DCA
DTW
Jul 19
MDW
as low as
$183
New York City, US (NYC) - Chicago, US (CHI)
Jun 30
LGA
1h 20m
Direct
Jun 30
MDW
as low as
$194
Flights to Chicago
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Flights From Chicago Midway Airport To New York City