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Cheap flights from Connecticut to Chicago from $37

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Connecticut to Chicago departing on 1/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Connecticut to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Connecticut to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Connecticut to Chicago.

Cheap last minute flights

Planning a quick getaway from Connecticut to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Connecticut to Chicago

Find recent round-trip train or bus tickets from Connecticut to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
10:59 am - 12:39 pmLGA-ORD
2h 40mnonstop
7:00 am - 10:04 amORD-LGA
2h 04mnonstop
$75Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 22
9:19 am - 11:06 amEWR-ORD
2h 47mnonstop
5:15 am - 8:24 amORD-EWR
2h 09mnonstop
$77Spirit Airlines
Find Deal
Mon, Feb 24 - Wed, Feb 26
10:59 am - 4:16 pmLGA-MDW
6h 17m1 stop
8:12 am - 3:00 pmMDW-LGA
5h 48m1 stop
$89Frontier
Find Deal
Tue, Feb 4 - Wed, Feb 12
11:00 am - 4:16 pmJFK-MDW
6h 16m1 stop
4:20 pm - 10:15 amMDW-JFK
16h 55m1 stop
$90Frontier
Find Deal
Tue, Feb 4 - Wed, Feb 12
7:59 am - 9:34 amEWR-ORD
2h 35mnonstop
12:42 pm - 9:10 pmORD-EWR
7h 28m1 stop
Mon, Jan 13 - Wed, Jan 15
10:59 am - 12:39 pmLGA-ORD
2h 40mnonstop
5:28 pm - 4:00 pmORD-LGA
21h 32m1 stop
Wed, Jan 22 - Mon, Jan 27
7:00 am - 8:46 amEWR-ORD
2h 46mnonstop
6:20 pm - 9:32 pmORD-EWR
2h 12mnonstop
$143American Airlines
Find Deal
Sun, Feb 2 - Wed, Feb 5
8:00 am - 9:40 amEWR-ORD
2h 40mnonstop
12:51 pm - 4:07 pmORD-EWR
2h 16mnonstop
$144United Airlines
Find Deal
Wed, Jan 29 - Wed, Feb 5
7:00 am - 8:46 amEWR-ORD
2h 46mnonstop
8:40 am - 11:56 amORD-EWR
2h 16mnonstop
$147American Airlines
Find Deal
Thu, Jan 23 - Tue, Jan 28
2:45 pm - 4:26 pmEWR-ORD
2h 41mnonstop
6:00 am - 9:11 amORD-EWR
2h 11mnonstop
$157United Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 21
10:59 am - 12:39 pmLGA-ORD
2h 40mnonstop
$37Spirit Airlines
Find Deal
Tue, Jan 21
7:59 am - 9:34 amEWR-ORD
2h 35mnonstop
$38Spirit Airlines
Find Deal
Fri, Jan 10
10:59 pm - 7:32 amLGA-MDW
9h 33m1 stop
$48Frontier
Find Deal
Mon, Feb 24
11:00 am - 4:16 pmJFK-MDW
6h 16m1 stop
$49Frontier
Find Deal
Tue, Feb 4
9:15 am - 10:59 amJFK-ORD
2h 44mnonstop
$74JetBlue
Find Deal
Tue, Mar 4
6:43 pm - 8:25 pmEWR-ORD
2h 42mnonstop
$74United Airlines
Find Deal
Tue, Feb 4
9:45 pm - 11:15 pmLGA-MDW
2h 30mnonstop
$74Southwest
Find Deal
Mon, Mar 10
10:03 am - 11:46 amEWR-ORD
2h 43mnonstop
$75United Airlines
Find Deal
Tue, Apr 1
6:30 am - 7:55 amLGA-MDW
2h 25mnonstop
$75Southwest
Find Deal
Thu, Mar 27
2:55 pm - 4:45 pmJFK-ORD
2h 50mnonstop
$79JetBlue
Find Deal
Tue, Feb 18
9:05 pm - 10:43 pmLGA-ORD
2h 38mnonstop
7:00 am - 10:04 amORD-LGA
2h 04mnonstop
$107Spirit Airlines
Find Deal
Mon, Jan 6 - Mon, Jan 13
9:05 pm - 10:43 pmLGA-ORD
2h 38mnonstop
5:06 pm - 8:10 pmORD-LGA
2h 04mnonstop
$119Spirit Airlines
Find Deal
Mon, Jan 6 - Sat, Jan 11
9:05 pm - 10:43 pmLGA-ORD
2h 38mnonstop
8:38 am - 3:10 pmORD-LGA
5h 32m1 stop
Mon, Jan 6 - Mon, Jan 13
7:30 am - 9:26 amJFK-ORD
2h 56mnonstop
5:05 pm - 8:31 pmORD-JFK
2h 26mnonstop
$194JetBlue
Find Deal
Mon, Jan 6 - Mon, Jan 13
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$196Southwest
Find Deal
Mon, Jan 6 - Mon, Jan 13
5:35 pm - 7:19 pmEWR-ORD
2h 44mnonstop
8:38 am - 9:10 pmORD-EWR
11h 32m1 stop
Mon, Jan 6 - Mon, Jan 13
9:37 am - 1:08 pmEWR-MDW
4h 31m1 stop
6:28 pm - 11:09 pmMDW-EWR
3h 41m1 stop
$213Delta
Find Deal
Mon, Jan 6 - Mon, Jan 13
7:30 am - 9:26 amJFK-ORD
2h 56mnonstop
5:05 pm - 8:31 pmORD-JFK
2h 26mnonstop
$221JetBlue
Find Deal
Mon, Jan 6 - Fri, Jan 10
8:45 pm - 10:36 pmLGA-ORD
2h 51mnonstop
5:15 pm - 8:33 pmORD-LGA
2h 18mnonstop
$221Delta
Find Deal
Mon, Jan 6 - Sat, Jan 11
6:00 am - 12:15 pmLGA-MDW
7h 15m1 stop
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
$240Southwest
Find Deal
Mon, Jan 6 - Mon, Jan 13
10:59 am - 12:39 pmLGA-ORD
2h 40mnonstop
7:00 am - 10:04 amORD-LGA
2h 04mnonstop
$75Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 22
9:19 am - 11:06 amEWR-ORD
2h 47mnonstop
5:15 am - 8:24 amORD-EWR
2h 09mnonstop
$77Spirit Airlines
Find Deal
Mon, Feb 24 - Wed, Feb 26
7:00 am - 8:46 amEWR-ORD
2h 46mnonstop
6:20 pm - 9:32 pmORD-EWR
2h 12mnonstop
$139American Airlines
Find Deal
Tue, Feb 4 - Sat, Feb 8
7:00 am - 8:46 amEWR-ORD
2h 46mnonstop
6:20 pm - 9:32 pmORD-EWR
2h 12mnonstop
$140American Airlines
Find Deal
Tue, Feb 4 - Wed, Feb 12
8:00 am - 9:40 amEWR-ORD
2h 40mnonstop
12:51 pm - 4:07 pmORD-EWR
2h 16mnonstop
$144United Airlines
Find Deal
Wed, Jan 29 - Wed, Feb 5
3:28 pm - 5:18 pmJFK-ORD
2h 50mnonstop
5:05 pm - 8:31 pmORD-JFK
2h 26mnonstop
$146JetBlue
Find Deal
Mon, Jan 20 - Fri, Jan 24
3:28 pm - 5:18 pmJFK-ORD
2h 50mnonstop
5:05 pm - 8:31 pmORD-JFK
2h 26mnonstop
$147JetBlue
Find Deal
Fri, Jan 24 - Mon, Jan 27
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
$147Southwest
Find Deal
Thu, Jan 30 - Sun, Feb 2
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
6:00 am - 9:10 amMDW-LGA
2h 10mnonstop
$148Southwest
Find Deal
Thu, Jan 23 - Mon, Jan 27
10:00 am - 11:38 amEWR-ORD
2h 38mnonstop
9:10 am - 12:28 pmORD-EWR
2h 18mnonstop
$169United Airlines
Find Deal
Wed, Jan 15 - Thu, Jan 16

Spirit Airlines flights from Connecticut to Chicago

Our best Spirit Airlines deals on Connecticut to Chicago flight tickets
Spirit Airlines
Jan 9
LGA10:59 amNew York LaGuardia
2h 40m
ORD12:39 pmChicago O'Hare Intl
Jan 13
ORD5:06 pmChicago O'Hare Intl
2h 04m
LGA8:10 pmNew York LaGuardia
Spirit Airlines
Jan 21
LGA10:59 amNew York LaGuardia
2h 40m
ORD12:39 pmChicago O'Hare Intl
Jan 22
ORD7:00 amChicago O'Hare Intl
2h 04m
LGA10:04 amNew York LaGuardia
Spirit Airlines
Feb 24
EWR9:19 amNewark
2h 47m
ORD11:06 amChicago O'Hare Intl
Feb 26
ORD5:15 amChicago O'Hare Intl
2h 09m
EWR8:24 amNewark

American Airlines flights from Connecticut to Chicago

Our best American Airlines deals on Connecticut to Chicago flight tickets
American Airlines
Feb 2
EWR7:00 amNewark
2h 46m
ORD8:46 amChicago O'Hare Intl
Feb 5
ORD6:20 pmChicago O'Hare Intl
2h 12m
EWR9:32 pmNewark
American Airlines
Jan 23
EWR7:00 amNewark
2h 46m
ORD8:46 amChicago O'Hare Intl
Jan 28
ORD8:40 amChicago O'Hare Intl
2h 16m
EWR11:56 amNewark
American Airlines
Jan 21
EWR12:35 pmNewark
2h 40m
ORD2:15 pmChicago O'Hare Intl
Jan 28
ORD2:50 pmChicago O'Hare Intl
2h 08m
EWR5:58 pmNewark

See travel insights to Chicago from

How to get the cheapest flight ticket from Connecticut 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 Connecticut to Chicago flight route?

Fly from Tweed-New Haven to Chicago Midway for the best Connecticut - Chicago flight prices

What cabin class options are available on Connecticut to Chicago flights?

There are 4 cabin classes available to choose from on Connecticut to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Connecticut to Chicago flights?

You could potentially save up to 24% on your flight if you consider stops on a Connecticut to Chicago flight.

Cheap Connecticut to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Connecticut to Chicago

Best Price Found

$37

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Connecticut in the past 72 hours is $37. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $75.
The fastest flight from Connecticut to Chicago takes 2h 15m
Direct flights go from Connecticut to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • When did momondo last update prices for flights from Connecticut to Chicago?

    Prices for flights from Connecticut to Chicago are updated daily.

  • How many operators does momondo search for flights from Connecticut to Chicago?

  • How old do you have to be to fly from Connecticut to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Connecticut to Chicago?


Best airlines flying from Connecticut to Chicago

Compare and see reviews for airlines that fly from Connecticut to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Avelo AirlinesPriceFrom $77Free CancellationRating
7.5
74 reviews
Search Avelo Airlines flights
FrontierPriceFrom $108Free CancellationRating
6.0
3,453 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $117Free CancellationRating
6.3
8,103 reviews
Search Spirit Airlines flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,537 reviews
Search Delta flights
American AirlinesPriceFrom $196Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $216Free CancellationRating
7.4
8,974 reviews
Search United Airlines flights
SouthwestPriceFrom $232Free CancellationRating
8.1
4,699 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Connecticut to Chicago?

Finding the right flight to Chicago from Connecticut is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Connecticut to Chicago with flexible booking policies on momondo?

All flight searches from Connecticut to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Connecticut to Chicago?

Once all potential Connecticut to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Connecticut to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Connecticut to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago