Cheap flights from New Windsor to Chicago from $47

Round-trip
1 adult
Economy
From?
To?
Tue 10/26
Tue 11/2

Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from New Windsor Stewart to Chicago.
View current United States travel restrictions

Flight information for New Windsor to Chicago
(SWF to CHI)

Find info about flight duration, direct flights, and airports for your flight from New Windsor to Chicago
Best Price Found$221The best flight deal from New Windsor to Chicago found on momondo in the last 72 hours is $221
Fastest flight time7h 35mThe fastest flight from New Windsor to Chicago takes 7h 35m
Direct flightsNoneThere are no direct flights from New Windsor to Chicago. Popular non-direct routes for this connection are New Windsor Stewart Airport - Chicago Midway Airport, New Windsor Stewart Airport - Chicago O'Hare Intl Airport and New Windsor Stewart Airport - Chicago Greater Rockford Airport.
Airports in Chicago3 airportsThere are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from New Windsor to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from New Windsor to Chicago?

July

The cheapest time of year to fly to Chicago from New Windsor is July. Most expensive is May

What is the cheapest day to depart New Windsor for Chicago?

Saturday

The cheapest day of the week is typically Saturday. The most expensive is typically Monday

When is the cheapest time to fly from New Windsor to Chicago?

in the morning

New Windsor to Chicago flights are approximately 34% more expensive in the afternoon than in the morning

What is the cheapest airline that flies to Chicago from New Windsor?

United Airlines

American Airlines, Delta, and United Airlines are the most popular carriers operating from New Windsor to Chicago

What is the cheapest New Windsor to Chicago flight route?

New Windsor Stewart - Chicago O'Hare Intl

Fly from New Windsor Stewart to Chicago O'Hare Intl for the best New Windsor - Chicago flight prices

How far in advance should you book New Windsor to Chicago flights?

58 days before

The cheapest time to buy a flight from New Windsor to Chicago is approximately 58 days to departure


Easily compare round-trip flights from New Windsor to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from New Windsor to Chicago by changing tabs
Multiple Airlines
Dec 3
SWF5:35 amNew Windsor Stewart
14h 36m
1 stop
ORD8:11 pmChicago O'Hare Intl
Dec 4
ORD5:23 amChicago O'Hare Intl
6h 51m
1 stop
SWF12:14 pmNew Windsor Stewart
Frontier
Nov 2
SWF10:02 amNew Windsor Stewart
9h 56m
1 stop
ORD7:58 pmChicago O'Hare Intl
Nov 4
ORD4:02 pmChicago O'Hare Intl
12h 46m
1 stop
SWF4:48 amNew Windsor Stewart
Allegiant Air
Nov 19
SWF1:48 pmNew Windsor Stewart
23h 23m
1 stop
RFD1:11 pmChicago Greater Rockford
Nov 21
RFD3:10 pmChicago Greater Rockford
11h 40m
1 stop
SWF2:50 amNew Windsor Stewart
Multiple Airlines
Nov 4
SWF8:51 amNew Windsor Stewart
10h 37m
1 stop
ORD7:28 pmChicago O'Hare Intl
Nov 7
ORD12:40 pmChicago O'Hare Intl
15h 08m
1 stop
SWF3:48 amNew Windsor Stewart
Multiple Airlines
Dec 1
SWF5:35 amNew Windsor Stewart
14h 35m
1 stop
ORD8:10 pmChicago O'Hare Intl
Dec 4
ORD5:23 amChicago O'Hare Intl
6h 51m
1 stop
SWF12:14 pmNew Windsor Stewart
Multiple Airlines
Nov 4
SWF8:51 amNew Windsor Stewart
10h 37m
1 stop
ORD7:28 pmChicago O'Hare Intl
Nov 7
ORD12:40 pmChicago O'Hare Intl
15h 08m
1 stop
SWF3:48 amNew Windsor Stewart

Find the cheapest one-way flights from New Windsor to Chicago

If you're looking for one-way flights from New Windsor to Chicago, view some of our deals below provided by Frontier
Frontier
Nov 10
SWF5:33 amNew Windsor Stewart
14h 36m
1 stop
ORD8:09 pmChicago O'Hare Intl
Multiple Airlines
Nov 1
SWF2:57 pmNew Windsor Stewart
26h 34m
1 stop
ORD5:31 pmChicago O'Hare Intl
Frontier
Nov 4
SWF8:51 amNew Windsor Stewart
10h 37m
1 stop
ORD7:28 pmChicago O'Hare Intl

Search last-minute flights to Chicago from New Windsor

Find and compare flight prices for your last-minute flight from New Windsor to Chicago
Multiple Airlines
Oct 29
SWF12:34 pmNew Windsor Stewart
28h 57m
1 stop
ORD5:31 pmChicago O'Hare Intl
Nov 1
ORD3:24 amChicago O'Hare Intl
9h 48m
1 stop
SWF1:12 pmNew Windsor Stewart
Multiple Airlines
Oct 29
SWF12:34 pmNew Windsor Stewart
16h 34m
2 stops
ORD5:08 amChicago O'Hare Intl
Nov 1
ORD3:24 amChicago O'Hare Intl
9h 48m
1 stop
SWF1:12 pmNew Windsor Stewart
Multiple Airlines
Oct 31
SWF2:18 pmNew Windsor Stewart
19h 14m
1 stop
ORD9:32 amChicago O'Hare Intl
Nov 4
ORD3:00 amChicago O'Hare Intl
9h 39m
1 stop
SWF12:39 pmNew Windsor Stewart
Multiple Airlines
Oct 29
SWF12:34 pmNew Windsor Stewart
16h 34m
2 stops
ORD5:08 amChicago O'Hare Intl
Nov 1
ORD3:24 amChicago O'Hare Intl
9h 48m
1 stop
SWF1:12 pmNew Windsor Stewart
Multiple Airlines
Oct 29
SWF12:34 pmNew Windsor Stewart
16h 34m
2 stops
ORD5:08 amChicago O'Hare Intl
Nov 1
ORD3:24 amChicago O'Hare Intl
9h 48m
1 stop
SWF1:12 pmNew Windsor Stewart
Multiple Airlines
Oct 31
SWF2:18 pmNew Windsor Stewart
19h 14m
1 stop
ORD9:32 amChicago O'Hare Intl
Nov 3
ORD3:45 amChicago O'Hare Intl
32h 54m
3 stops
SWF12:39 pmNew Windsor Stewart

Best airlines flying from New Windsor to Chicago

Compare and see reviews for airlines that fly from New Windsor to Chicago with momondo
AirlineRatingFree CancellationPrice
Delta
PriceFrom $91
Free Cancellation
Rating
8.2
8.2

Boarding

8.4

Comfort

8.3

Crew

8.1

Entertainment

8.0

Food

Reviews

Great

1 / 10
United Airlines
PriceFrom $95
Free Cancellation
Rating
6.9
7.3

Boarding

6.7

Comfort

7.5

Crew

6.7

Entertainment

6.2

Food

Reviews

Pros: Everything! From ticketing agent to all the crew on our flight back were awesome. Thank you!

1 / 10
American Airlines
PriceFrom $123
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.1

Entertainment

6.8

Food

Reviews

Flight attendant for first class is definitely not a morning person. Oh and the WiFi DID NOT WORK!

1 / 10

  • Are airlines flying from New Windsor Stewart to Chicago offering flexible cancellation due to COVID-19?

    Due to the global impact of COVID-19, some of our airline partners operating flights from New Windsor Stewart to Chicago, such as Delta, American Airlines, and United Airlines may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.

  • How far is New Windsor Stewart to Chicago by plane?

    There are 701.4 mi between New Windsor Stewart and Chicago. Flights usually cover this in 8h 32m, depending on flying conditions and air traffic around both airports.


Can I fly to Chicago from New Windsor Stewart right now?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from New Windsor Stewart need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from New Windsor Stewart must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from New Windsor Stewart are not required to quarantine after entering Chicago.

Can I fly back to New Windsor Stewart from Chicago?

Returning to New Windsor Stewart from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to New Windsor Stewart.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering New Windsor Stewart.

If you are planning to travel to Chicago at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

Alternative routes for New Windsor to Chicago

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