Cheap flights from Chicago (CHI) to New Windsor (SWF) from $97

This is the cheapest one-way flight price, found on 5/24. Prices may vary by date and flight preferences.
CHI — SWF
May 30 — Jun 61

Cheap flights from Chicago to Stewart in May, June 2023

The best prices found for CHI to SWF flights for May, June

Chicago to Stewart 2023 flight deals

Cheap flights to Stewart from Chicago found for this year

Cheap Undisclosed Carrier flights from Chicago to Stewart

Last minute flights from Chicago to Stewart

Late deals on return flights to Stewart from Chicago, departing today and this week

One-way flights to Stewart from Chicago

The cheapest one-way flights from Chicago to Stewart

Find flights from Chicago to Stewart within your budget

Use the slider to find flights from Chicago to Stewart that fit your budget.

Fly from

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Fly to

Any airport

Budget

$366 - $690

Route

Depart

Return

Price

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 6/28

3 stops36h 51m

New Windsor Stewart

Fri 6/30

3 stops35h 35m

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 6/25

1 stop8h 07m

New Windsor Stewart

Thu 6/29

1 stop9h 09m

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 6/11

1 stop8h 07m

New Windsor Stewart

Thu 6/15

1 stop8h 59m

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 6/28

1 stop13h 14m

New Windsor Stewart

Fri 6/30

3 stops35h 35m

Chicago MidwayNew Windsor Stewart

MDW - SWF

MDWSWF

Chicago Midway

Wed 6/14

2 stops16h 32m

New Windsor Stewart

Mon 6/26

3 stops35h 44m

Chicago MidwayNew Windsor Stewart

MDW - SWF

MDWSWF

Chicago Midway

Wed 6/14

2 stops20h 01m

New Windsor Stewart

Mon 6/26

2 stops48h 17m

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 6/28

1 stop13h 14m

New Windsor Stewart

Fri 6/30

2 stops47h 22m

Chicago MidwayNew Windsor Stewart

MDW - SWF

MDWSWF

Chicago Midway

Thu 7/6

3 stops45h 08m

New Windsor Stewart

Sun 7/9

2 stops18h 13m

Chicago O'Hare IntlNew Windsor Stewart

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 8/5

3 stops28h 41m

New Windsor Stewart

Sun 8/13

3 stops24h 06m

Flights are sorted by cheapest first

Deals found on 5/24

Reviews of Airlines Servicing Stewart

Allegiant Air
7.5
Good
100 reviews

Comfort

6.9

Boarding

7.8

Crew

8.3

Entertainment

5.6

Overall

7.5

Food

6.1

Reviews

1 / 10

Baggage. They looked at our bags and said we could use them as carry ins, charged us and then later said they were too big and charged us more to check them

Allegiant Air
7.5
Good
100 reviews
Allegiant Air
7.5
Good
100 reviews

Comfort

6.9

Boarding

7.8

Crew

8.3

Entertainment

5.6

Overall

7.5

Food

6.1

Reviews

1 / 10

Baggage. They looked at our bags and said we could use them as carry ins, charged us and then later said they were too big and charged us more to check them

Frontier
5.9
Fair
642 reviews
Allegiant Air
7.5
Good
100 reviews

Comfort

6.9

Boarding

7.8

Crew

8.3

Entertainment

5.6

Overall

7.5

Food

6.1

Reviews

1 / 10

Baggage. They looked at our bags and said we could use them as carry ins, charged us and then later said they were too big and charged us more to check them

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