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Cheap flights from Connecticut to Chicago from $70

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 2/4. 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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0 bags

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Find the cheapest flights from Connecticut to Chicago

Cheap round-trip flights

Frontier Logo
11:00 am - 12:45 pmJFK-ORD
2h 45mnonstop
Frontier Logo
6:40 am - 10:03 amORD-JFK
2h 23mnonstop
$126Frontier
Find Deal
Fri, Oct 24 - Tue, Nov 4
Spirit Airlines Logo
11:59 am - 11:45 pmLGA-ORD
12h 46m1 stop
Spirit Airlines Logo
11:13 am - 2:08 pmORD-LGA
1h 55mnonstop
$126Spirit Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Multiple Airlines Logo
3:29 pm - 5:13 pmLGA-ORD
2h 44mnonstop
Multiple Airlines Logo
12:28 pm - 10:44 pmORD-LGA
9h 16m1 stop
$127Multiple Airlines
Find Deal
Wed, Oct 15 - Fri, Oct 17
Multiple Airlines Logo
11:59 am - 6:38 pmLGA-ORD
7h 39m1 stop
Multiple Airlines Logo
12:28 pm - 10:44 pmORD-LGA
9h 16m1 stop
$128Multiple Airlines
Find Deal
Wed, Oct 15 - Fri, Oct 17
JetBlue Logo
10:30 am - 12:22 pmJFK-ORD
2h 52mnonstop
JetBlue Logo
6:45 am - 9:59 amORD-JFK
2h 14mnonstop
$137JetBlue
Find Deal
Tue, Oct 21 - Wed, Oct 29
Southwest Logo
9:45 pm - 11:10 pmLGA-MDW
2h 25mnonstop
Southwest Logo
8:25 am - 11:30 amMDW-LGA
2h 05mnonstop
$137Southwest
Find Deal
Tue, Oct 28 - Wed, Oct 29
Southwest Logo
8:15 am - 9:40 amLGA-MDW
2h 25mnonstop
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$147Southwest
Find Deal
Sat, Oct 25 - Mon, Oct 27
American Airlines Logo
12:26 pm - 2:15 pmJFK-ORD
2h 49mnonstop
American Airlines Logo
4:06 pm - 7:27 pmORD-JFK
2h 21mnonstop
$152American Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 8
JetBlue Logo
7:00 pm - 8:52 pmJFK-ORD
2h 52mnonstop
JetBlue Logo
9:00 am - 12:17 pmORD-JFK
2h 17mnonstop
$159JetBlue
Find Deal
Fri, Nov 14 - Tue, Jan 13
American Airlines Logo
9:00 am - 10:51 amJFK-ORD
2h 51mnonstop
American Airlines Logo
10:06 am - 1:29 pmORD-JFK
2h 23mnonstop
$168American Airlines
Find Deal
Thu, Nov 6 - Thu, Dec 4

Frontier flights from Connecticut to Chicago

Our best Frontier deals on Connecticut to Chicago flight tickets
Frontier
Oct 24
JFK11:00 amNew York John F Kennedy Intl
2h 45m
ORD12:45 pmChicago O'Hare Intl
Nov 4
ORD6:40 amChicago O'Hare Intl
2h 23m
JFK10:03 amNew York John F Kennedy Intl
$126
Find similar
Frontier
Oct 11
JFK12:59 pmNew York John F Kennedy Intl
12h 00m
1 stop
ORD11:59 pmChicago O'Hare Intl
Oct 15
ORD6:40 amChicago O'Hare Intl
2h 23m
JFK10:03 amNew York John F Kennedy Intl
$127
Find similar
Frontier
Oct 31
JFK11:00 amNew York John F Kennedy Intl
2h 45m
ORD12:45 pmChicago O'Hare Intl
Nov 2
ORD5:40 amChicago O'Hare Intl
2h 23m
JFK9:03 amNew York John F Kennedy Intl
$128
Find similar

Spirit Airlines flights from Connecticut to Chicago

Our best Spirit Airlines deals on Connecticut to Chicago flight tickets
Spirit Airlines
Oct 14
LGA11:59 amNew York LaGuardia
12h 46m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 21
ORD11:13 amChicago O'Hare Intl
1h 55m
LGA2:08 pmNew York LaGuardia
$126
Find similar
Spirit Airlines
Sep 27
LGA8:36 pmNew York LaGuardia
2h 35m
ORD10:11 pmChicago O'Hare Intl
Oct 7
ORD11:13 amChicago O'Hare Intl
1h 55m
LGA2:08 pmNew York LaGuardia
$127
Find similar
Spirit Airlines
Oct 15
LGA11:59 amNew York LaGuardia
7h 39m
1 stop
ORD6:38 pmChicago O'Hare Intl
Oct 16
ORD11:13 amChicago O'Hare Intl
1h 55m
LGA2:08 pmNew York LaGuardia
$129
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Connecticut to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 21, 2025.
Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Fri 10/24

11:00 am-12:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Tue 11/4

6:40 am-10:03 am

Nonstop2h 23m

$126

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 10/14

11:59 am-11:45 pm

1 stop12h 46m

Chicago O'Hare Intl

Tue 10/21

11:13 am-2:08 pm

Nonstop1h 55m

$126

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/15

3:29 pm-5:13 pm

Nonstop2h 44m

Chicago O'Hare Intl

Fri 10/17

12:28 pm-10:44 pm

1 stop9h 16m

$127

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/15

11:59 am-6:38 pm

1 stop7h 39m

Chicago O'Hare Intl

Fri 10/17

12:28 pm-10:44 pm

1 stop9h 16m

$128

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 10/21

10:30 am-12:22 pm

Nonstop2h 52m

Chicago O'Hare Intl

Wed 10/29

6:45 am-9:59 am

Nonstop2h 14m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/28

9:45 pm-11:10 pm

Nonstop2h 25m

Chicago Midway

Wed 10/29

8:25 am-11:30 am

Nonstop2h 05m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 10/25

8:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Mon 10/27

8:20 pm-11:25 pm

Nonstop2h 05m

$147

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 11/8

12:26 pm-2:15 pm

Nonstop2h 49m

Chicago O'Hare Intl

Sat 11/8

4:06 pm-7:27 pm

Nonstop2h 21m

$152

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Fri 11/14

7:00 pm-8:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Tue 1/13

9:00 am-12:17 pm

Nonstop2h 17m

$159

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 11/6

9:00 am-10:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Thu 12/4

10:06 am-1:29 pm

Nonstop2h 23m

$168

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Connecticut, with most prices found around $307. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Connecticut to Chicago during September average around $318.

What is the cheapest Connecticut to Chicago flight route?

Fly from Tweed-New Haven to Chicago O'Hare Intl 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?

No. A direct flight is the cheapest option for a flight between Connecticut to Chicago.

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

$179

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Connecticut in the past 72 hours is $179. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $178.
The fastest flight from Connecticut to Chicago takes 2h 20m
Direct flights go from Connecticut to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • 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
FrontierPriceFrom $115Free CancellationRating
5.8
3,166 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
American AirlinesPriceFrom $185Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $231Free CancellationRating
7.4
8,922 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport