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Cheap flights from Connecticut to Chicago from $43

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 12/10. 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.
8:36 am - 10:17 amLGA-ORD
2h 41mnonstop
4:19 pm - 7:24 pmORD-LGA
2h 05mnonstop
$86Spirit Airlines
Find Deal
Tue, Dec 10 - Tue, Dec 17
10:55 pm - 12:34 amEWR-ORD
2h 39mnonstop
6:37 pm - 9:55 pmORD-EWR
2h 18mnonstop
$88Spirit Airlines
Find Deal
Tue, Dec 10 - Tue, Dec 17
10:00 pm - 9:04 amLGA-ORD
12h 04m1 stop
2:59 pm - 10:00 pmORD-LGA
6h 01m1 stop
$100Frontier
Find Deal
Sat, Jan 25 - Tue, Jan 28
8:35 am - 10:07 amLGA-ORD
2h 32mnonstop
3:00 pm - 10:00 pmORD-LGA
6h 00m1 stop
Tue, Jan 7 - Tue, Jan 14
5:00 pm - 9:52 amLGA-ORD
17h 52m1 stop
5:06 pm - 8:10 pmORD-LGA
2h 04mnonstop
Sat, Jan 25 - Tue, Jan 28
10:59 am - 4:16 pmLGA-MDW
6h 17m1 stop
6:45 am - 5:00 pmMDW-LGA
9h 15m1 stop
$118Frontier
Find Deal
Tue, Jan 28 - Fri, Jan 31
7:00 am - 8:46 amEWR-ORD
2h 46mnonstop
6:20 pm - 9:32 pmORD-EWR
2h 12mnonstop
$139American Airlines
Find Deal
Tue, Jan 14 - Tue, Jan 21
7:00 am - 8:46 amEWR-ORD
2h 46mnonstop
2:50 pm - 5:58 pmORD-EWR
2h 08mnonstop
$143American Airlines
Find Deal
Fri, Jan 24 - Tue, Jan 28
3:28 pm - 5:18 pmJFK-ORD
2h 50mnonstop
5:05 pm - 8:31 pmORD-JFK
2h 26mnonstop
$146JetBlue
Find Deal
Thu, Jan 9 - Sun, Jan 12
3:28 pm - 5:18 pmJFK-ORD
2h 50mnonstop
5:05 pm - 8:31 pmORD-JFK
2h 26mnonstop
$147JetBlue
Find Deal
Fri, Jan 17 - Mon, Jan 20
10:55 pm - 12:34 amEWR-ORD
2h 39mnonstop
$43Spirit Airlines
Find Deal
Tue, Dec 10
10:55 pm - 12:34 amEWR-ORD
2h 39mnonstop
$44Spirit Airlines
Find Deal
Wed, Dec 11
11:01 am - 4:56 pmJFK-ORD
6h 55m1 stop
$49Frontier
Find Deal
Wed, Feb 12
11:00 am - 4:14 pmJFK-MDW
6h 14m1 stop
$49Frontier
Find Deal
Tue, Jan 7
3:28 pm - 5:18 pmJFK-ORD
2h 50mnonstop
$74JetBlue
Find Deal
Mon, Jan 13
3:00 pm - 4:40 pmEWR-ORD
2h 40mnonstop
$74American Airlines
Find Deal
Tue, Jan 14
9:20 am - 11:01 amLGA-ORD
2h 41mnonstop
$74United Airlines
Find Deal
Thu, Jan 16
2:55 pm - 4:45 pmJFK-ORD
2h 50mnonstop
$79JetBlue
Find Deal
Tue, Feb 18
7:29 pm - 11:15 pmLGA-ORD
4h 46m1 stop
$83United Airlines
Find Deal
Mon, Jan 13
9:00 am - 11:00 amJFK-ORD
3h 00mnonstop
$98American Airlines
Find Deal
Tue, Dec 3
8:35 am - 10:05 amLGA-ORD
2h 30mnonstop
10:43 am - 2:00 pmORD-LGA
2h 17mnonstop
$211Spirit Airlines
Find Deal
Tue, Nov 26 - Tue, Dec 10
8:29 pm - 10:06 pmLGA-ORD
2h 37mnonstop
4:19 pm - 7:24 pmORD-LGA
2h 05mnonstop
$219Spirit Airlines
Find Deal
Thu, Nov 28 - Fri, Dec 6
8:35 am - 10:05 amLGA-ORD
2h 30mnonstop
6:07 pm - 10:00 amORD-LGA
14h 53m1 stop
Wed, Nov 27 - Mon, Dec 16
2:12 pm - 10:14 pmBDL-ORD
9h 02m1 stop
8:27 pm - 10:02 pmORD-BDL
24h 35m1 stop
Thu, Nov 28 - Tue, Dec 3
8:00 am - 2:24 pmEWR-ORD
7h 24m1 stop
6:20 pm - 9:32 pmORD-EWR
2h 12mnonstop
$302American Airlines
Find Deal
Sat, Nov 30 - Fri, Jan 10
7:23 am - 9:01 amLGA-ORD
2h 38mnonstop
8:00 pm - 11:12 pmORD-LGA
2h 12mnonstop
$317United Airlines
Find Deal
Wed, Nov 27 - Wed, Dec 4
7:30 am - 9:18 amLGA-ORD
2h 48mnonstop
6:45 am - 10:03 amORD-LGA
2h 18mnonstop
$329Delta
Find Deal
Fri, Nov 29 - Sun, Dec 8
9:00 am - 11:00 amJFK-ORD
3h 00mnonstop
11:45 am - 3:00 pmORD-JFK
2h 15mnonstop
$335American Airlines
Find Deal
Wed, Nov 27 - Mon, Dec 16
6:00 pm - 7:54 pmLGA-ORD
2h 54mnonstop
5:53 pm - 9:05 pmORD-LGA
2h 12mnonstop
$347Delta
Find Deal
Tue, Nov 26 - Fri, Dec 6
2:55 pm - 7:54 amBDL-ORD
17h 59m2 stops
10:55 am - 2:07 pmORD-BDL
2h 12mnonstop
$408United Airlines
Find Deal
Thu, Nov 28 - Fri, Nov 29
8:36 am - 10:17 amLGA-ORD
2h 41mnonstop
4:19 pm - 7:24 pmORD-LGA
2h 05mnonstop
$86Spirit Airlines
Find Deal
Tue, Dec 10 - Tue, Dec 17
10:55 pm - 12:34 amEWR-ORD
2h 39mnonstop
6:37 pm - 9:55 pmORD-EWR
2h 18mnonstop
$88Spirit Airlines
Find Deal
Tue, Dec 10 - Tue, Dec 17
7:00 am - 8:46 amEWR-ORD
2h 46mnonstop
10:40 am - 1:54 pmORD-EWR
2h 14mnonstop
$134American Airlines
Find Deal
Wed, Jan 22 - Wed, Jan 22
7:00 am - 8:46 amEWR-ORD
2h 46mnonstop
10:40 am - 1:54 pmORD-EWR
2h 14mnonstop
$135American Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 8
3:28 pm - 5:18 pmJFK-ORD
2h 50mnonstop
5:05 pm - 8:31 pmORD-JFK
2h 26mnonstop
$146JetBlue
Find Deal
Thu, Jan 9 - Sun, Jan 12
3:28 pm - 5:18 pmJFK-ORD
2h 50mnonstop
5:05 pm - 8:31 pmORD-JFK
2h 26mnonstop
$147JetBlue
Find Deal
Fri, Jan 17 - Mon, Jan 20
7:25 am - 9:15 amLGA-ORD
2h 50mnonstop
7:40 pm - 11:00 pmORD-LGA
2h 20mnonstop
$147Delta
Find Deal
Fri, Jan 10 - Fri, Jan 17
6:00 am - 7:35 amLGA-MDW
2h 35mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$148Southwest
Find Deal
Fri, Jan 17 - Fri, Jan 24
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$153Southwest
Find Deal
Tue, Jan 7 - Wed, Feb 19
6:00 am - 7:43 amLGA-ORD
2h 43mnonstop
8:40 am - 11:55 amORD-LGA
2h 15mnonstop
$165Delta
Find Deal
Mon, Dec 16 - Wed, Dec 18

Delta flights from Connecticut to Chicago

Our best Delta deals on Connecticut to Chicago flight tickets
Delta
Jan 10
LGA7:25 amNew York LaGuardia
2h 50m
ORD9:15 amChicago O'Hare Intl
Jan 17
ORD7:40 pmChicago O'Hare Intl
2h 20m
LGA11:00 pmNew York LaGuardia
Delta
Feb 12
JFK8:00 amNew York John F Kennedy Intl
2h 55m
ORD9:55 amChicago O'Hare Intl
Feb 19
ORD7:05 amChicago O'Hare Intl
2h 26m
JFK10:31 amNew York John F Kennedy Intl
Delta
Jan 7
EWR1:00 pmNewark
6h 14m
1 stop
MDW6:14 pmChicago Midway
Jan 8
MDW6:00 amChicago Midway
5h 15m
1 stop
EWR12:15 pmNewark

JetBlue flights from Connecticut to Chicago

Our best JetBlue deals on Connecticut to Chicago flight tickets
JetBlue
Jan 9
JFK3:28 pmNew York John F Kennedy Intl
2h 50m
ORD5:18 pmChicago O'Hare Intl
Jan 12
ORD5:05 pmChicago O'Hare Intl
2h 26m
JFK8:31 pmNew York John F Kennedy Intl
JetBlue
Jan 17
JFK3:28 pmNew York John F Kennedy Intl
2h 50m
ORD5:18 pmChicago O'Hare Intl
Jan 20
ORD5:05 pmChicago O'Hare Intl
2h 26m
JFK8:31 pmNew York John F Kennedy Intl
JetBlue
Mar 2
JFK9:15 amNew York John F Kennedy Intl
2h 44m
ORD10:59 amChicago O'Hare Intl
Mar 10
ORD11:44 amChicago O'Hare Intl
2h 15m
JFK2:59 pmNew York John F Kennedy Intl

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 13% 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

$43

Fastest flight time

2h 25m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Connecticut in the past 72 hours is $43. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $86.
The fastest flight from Connecticut to Chicago takes 2h 25m
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
6.1
3,526 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $117Free CancellationRating
6.3
8,176 reviews
Search Spirit Airlines flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,734 reviews
Search Delta flights
SouthwestPriceFrom $190Free CancellationRating
8.1
4,984 reviews
Search Southwest flights
American AirlinesPriceFrom $192Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $210Free CancellationRating
7.4
9,156 reviews
Search United Airlines 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