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$50 Find cheap flights from New York to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 9/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 7/5
Fri 7/12

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In the last 7 days travelers have searched 44,281,614 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

June

Cheapest flight

$50
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from New York LaGuardia Airport to Chicago Midway Airport

FAQs for booking New York to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from New York State to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York State to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York State to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from New York State is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New York State to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to New York State with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York State to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from New York State up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from New York State to Chicago Midway Airport?

Find which airlines fly direct from New York State to Midway, which days they fly and book direct flights.

Nonstop departures

New York to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

See more direct flights

Nonstop returns

Chicago Midway to New York

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

See more direct flights
See more direct flights

Book cheap flights from New York State to Chicago

Recent round-trip flight deals

8/20Tue
1 stopFrontier
5h 50mLGA-MDW
8/28Wed
1 stopFrontier
10h 03mMDW-LGA
$106
9/4Wed
1 stopFrontier
16h 55mLGA-MDW
9/11Wed
1 stopFrontier
10h 03mMDW-LGA
$112
7/10Wed
nonstopSouthwest
2h 20mLGA-MDW
7/11Thu
nonstopSouthwest
2h 10mMDW-LGA
$149
9/14Sat
1 stopDelta
5h 14mEWR-MDW
9/18Wed
1 stopDelta
5h 20mMDW-EWR
$156
8/1Thu
nonstopSouthwest
2h 25mLGA-MDW
8/3Sat
1 stopSouthwest
5h 45mMDW-LGA
$158
11/13Wed
1 stopDelta
5h 04mEWR-MDW
11/16Sat
1 stopDelta
4h 09mMDW-EWR
$191
6/21Fri
1 stopAllegiant Air
10h 23mEWR-MDW
6/24Mon
1 stopAllegiant Air
11h 57mMDW-EWR
$246
6/21Fri
1 stopAllegiant Air
10h 23mEWR-MDW
6/24Mon
1 stopAllegiant Air
11h 57mMDW-EWR
$254
7/19Fri
1 stop
10h 22mEWR-MDW
7/22Mon
2 stops
23h 52mMDW-EWR
$295
7/19Fri
1 stop
10h 22mEWR-MDW
7/22Mon
3 stops
25h 03mMDW-EWR
$305

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Recent one-way flight deals

9/25Wed
1 stopFrontier
5h 29mLGA-MDW
$50
6/11Tue
1 stopFrontier
6h 07mLGA-MDW
$54
9/17Tue
1 stopDelta
5h 04mEWR-MDW
$78
8/28Wed
1 stopDelta
5h 25mEWR-MDW
$89
9/6Fri
1 stopAllegiant Air
9h 31mEWR-MDW
$109
7/10Wed
nonstopSouthwest
2h 25mLGA-MDW
$114
7/19Fri
1 stopAllegiant Air
10h 22mEWR-MDW
$122
7/10Wed
1 stopSouthwest
11h 30mLGA-MDW
$129
9/1Sun
2 stops
19h 14mLGA-MDW
$199
8/25Sun
3 stops
19h 23mLGA-MDW
$206

Search by stops

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Search by price

Last minute flights from New York to Midway

Last minute flight, train and bus deals

6/10Mon
multi-stopFrontier
6h 48mSYR-MDW
6/13Thu
multi-stopFrontier
11h 42mMDW-SYR
$126
6/10Mon
multi-stopFrontier
6h 48mSYR-MDW
6/13Thu
multi-stopFrontier
18h 21mMDW-SYR
$182
6/8Sat
multi-stopDelta
3h 08mROC-MDW
6/11Tue
multi-stopDelta
3h 21mMDW-ROC
$318
6/10Mon
nonstopSouthwest
2h 20mLGA-MDW
6/11Tue
nonstopSouthwest
2h 10mMDW-LGA
$326
6/10Mon
multi-stopSouthwest
10h 45mLGA-MDW
6/11Tue
nonstopSouthwest
2h 05mMDW-LGA
$335
6/7Fri
multi-stop
9h 49mEWR-MDW
6/14Fri
multi-stop
14h 05mMDW-EWR
$370
6/10Mon
multi-stopDelta
7h 55mEWR-MDW
6/13Thu
multi-stopDelta
5h 56mMDW-EWR
$372
6/10Mon
multi-stop
9h 49mEWR-MDW
6/14Fri
multi-stop
14h 05mMDW-EWR
$381
6/10Mon
multi-stopPorter Airlines
8h 27mEWR-MDW
6/11Tue
multi-stopPorter Airlines
5h 20mMDW-EWR
$807
6/7Fri
multi-stopPorter Airlines
8h 27mEWR-MDW
6/12Wed
multi-stopPorter Airlines
6h 35mMDW-EWR
$829

Search by stops

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