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Cheap flights from Connecticut to Chicago from $62

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 1/22. 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

Enter your travel dates to find the best prices.
Frontier Logo
1:00 pm - 2:57 pmJFK-ORD
2h 57mnonstop
Frontier Logo
11:44 am - 12:59 amORD-JFK
12h 15m1 stop
$95Frontier
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Fri, Dec 5 - Mon, Dec 8
Spirit Airlines Logo
8:41 pm - 10:11 pmLGA-ORD
2h 30mnonstop
Spirit Airlines Logo
4:38 pm - 7:42 pmORD-LGA
2h 04mnonstop
$95Spirit Airlines
Find Deal
Sat, Dec 13 - Mon, Dec 15
Multiple Airlines Logo
12:59 pm - 2:31 pmLGA-ORD
2h 32mnonstop
Multiple Airlines Logo
8:00 am - 4:29 pmORD-LGA
7h 29m1 stop
$99Multiple Airlines
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Wed, Nov 19 - Wed, Dec 10
Multiple Airlines Logo
8:41 pm - 10:11 pmLGA-ORD
2h 30mnonstop
Multiple Airlines Logo
11:01 am - 9:13 pmORD-LGA
9h 12m1 stop
$100Multiple Airlines
Find Deal
Sat, Dec 6 - Mon, Dec 8
American Airlines Logo
5:29 pm - 7:23 pmJFK-ORD
2h 54mnonstop
American Airlines Logo
10:06 am - 1:29 pmORD-JFK
2h 23mnonstop
$115American Airlines
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Thu, Dec 4 - Wed, Dec 10
Southwest Logo
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
Southwest Logo
7:15 pm - 10:20 pmMDW-LGA
2h 05mnonstop
$115Southwest
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Thu, Dec 4 - Wed, Dec 10
United Airlines Logo
9:01 am - 10:45 amEWR-ORD
2h 44mnonstop
United Airlines Logo
4:25 pm - 7:48 pmORD-EWR
2h 23mnonstop
$126United Airlines
Find Deal
Mon, Nov 24 - Wed, Dec 3
Southwest Logo
6:00 am - 7:30 amLGA-MDW
2h 30mnonstop
Southwest Logo
7:15 pm - 10:20 pmMDW-LGA
2h 05mnonstop
$132Southwest
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Fri, Dec 5 - Tue, Dec 9
United Airlines Logo
6:20 pm - 8:07 pmEWR-ORD
2h 47mnonstop
United Airlines Logo
6:00 am - 9:07 amORD-EWR
2h 07mnonstop
$132United Airlines
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Thu, Dec 4 - Sun, Dec 7
American Airlines Logo
5:29 pm - 7:23 pmJFK-ORD
2h 54mnonstop
American Airlines Logo
10:06 am - 1:29 pmORD-JFK
2h 23mnonstop
$135American Airlines
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Thu, Dec 4 - Mon, Dec 8

Spirit Airlines flights from Connecticut to Chicago

Our best Spirit Airlines deals on Connecticut to Chicago flight tickets
Spirit Airlines
Dec 13
LGA8:41 pmNew York LaGuardia
2h 30m
ORD10:11 pmChicago O'Hare Intl
Dec 15
ORD4:38 pmChicago O'Hare Intl
2h 04m
LGA7:42 pmNew York LaGuardia
$95
Find similar
Spirit Airlines
Dec 31
LGA8:37 pmNew York LaGuardia
2h 30m
ORD10:07 pmChicago O'Hare Intl
Jan 24
ORD6:19 pmChicago O'Hare Intl
2h 10m
LGA9:29 pmNew York LaGuardia
$96
Find similar
Spirit Airlines
Nov 20
LGA12:59 pmNew York LaGuardia
2h 32m
ORD2:31 pmChicago O'Hare Intl
Dec 18
ORD4:38 pmChicago O'Hare Intl
2h 04m
LGA7:42 pmNew York LaGuardia
$97
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American Airlines flights from Connecticut to Chicago

Our best American Airlines deals on Connecticut to Chicago flight tickets
American Airlines
Dec 4
JFK5:29 pmNew York John F Kennedy Intl
2h 54m
ORD7:23 pmChicago O'Hare Intl
Dec 10
ORD10:06 amChicago O'Hare Intl
2h 23m
JFK1:29 pmNew York John F Kennedy Intl
$115
Find similar
American Airlines
Dec 4
JFK5:29 pmNew York John F Kennedy Intl
2h 54m
ORD7:23 pmChicago O'Hare Intl
Dec 8
ORD10:06 amChicago O'Hare Intl
2h 23m
JFK1:29 pmNew York John F Kennedy Intl
$135
Find similar
American Airlines
Dec 12
EWR7:07 amNewark
2h 58m
ORD9:05 amChicago O'Hare Intl
Dec 13
ORD7:27 pmChicago O'Hare Intl
2h 14m
EWR10:41 pmNewark
$143
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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 November 6, 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 12/5

1:00 pm-2:57 pm

Nonstop2h 57m

Chicago O'Hare Intl

Mon 12/8

11:44 am-12:59 am

1 stop12h 15m

$95

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 12/13

8:41 pm-10:11 pm

Nonstop2h 30m

Chicago O'Hare Intl

Mon 12/15

4:38 pm-7:42 pm

Nonstop2h 04m

$95

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 11/19

12:59 pm-2:31 pm

Nonstop2h 32m

Chicago O'Hare Intl

Wed 12/10

8:00 am-4:29 pm

1 stop7h 29m

$99

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 12/6

8:41 pm-10:11 pm

Nonstop2h 30m

Chicago O'Hare Intl

Mon 12/8

11:01 am-9:13 pm

1 stop9h 12m

$100

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 12/4

5:29 pm-7:23 pm

Nonstop2h 54m

Chicago O'Hare Intl

Wed 12/10

10:06 am-1:29 pm

Nonstop2h 23m

$115

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 12/4

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Wed 12/10

7:15 pm-10:20 pm

Nonstop2h 05m

$115

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 11/24

9:01 am-10:45 am

Nonstop2h 44m

Chicago O'Hare Intl

Wed 12/3

4:25 pm-7:48 pm

Nonstop2h 23m

$126

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 12/5

6:00 am-7:30 am

Nonstop2h 30m

Chicago Midway

Tue 12/9

7:15 pm-10:20 pm

Nonstop2h 05m

$132

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 12/4

6:20 pm-8:07 pm

Nonstop2h 47m

Chicago O'Hare Intl

Sun 12/7

6:00 am-9:07 am

Nonstop2h 07m

$132

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 12/4

5:29 pm-7:23 pm

Nonstop2h 54m

Chicago O'Hare Intl

Mon 12/8

10:06 am-1:29 pm

Nonstop2h 23m

$135

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 September is, on average, the cheapest month to fly to Chicago from Connecticut, with most prices found around $301. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Connecticut to Chicago during August average around $307.

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

$49

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 $49. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $347.
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)
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  • 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 $97Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,241 reviews
Search Southwest flights
American AirlinesPriceFrom $185Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
United AirlinesPriceFrom $224Free CancellationRating
7.4
9,007 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
Portage
Lansing
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