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Cheap flights from Connecticut to Chicago from $94

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 7/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Connecticut to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
6:59 am - 8:47 am
JFK
-
ORD
2h 48mnonstop
JetBlue Logo
6:30 pm - 10:06 pm
ORD
-
JFK
2h 36mnonstop
$186JetBlue
Wed, Aug 5 - Wed, Aug 12
American Airlines Logo
9:46 pm - 11:42 pm
LGA
-
ORD
2h 56mnonstop
American Airlines Logo
3:04 pm - 6:22 pm
ORD
-
LGA
2h 18mnonstop
$186American Airlines
Sat, Aug 22 - Wed, Aug 26
United Airlines Logo
11:20 am - 12:57 pm
LGA
-
ORD
2h 37mnonstop
United Airlines Logo
6:00 pm - 9:25 pm
ORD
-
LGA
2h 25mnonstop
$187United Airlines
Wed, Jul 22 - Sat, Jul 25
Southwest Logo
9:30 pm - 11:00 pm
LGA
-
MDW
2h 30mnonstop
Southwest Logo
6:40 pm - 9:50 pm
MDW
-
LGA
2h 10mnonstop
$187Southwest
Wed, Jul 22 - Sat, Jul 25
JetBlue Logo
7:05 am - 8:50 am
JFK
-
ORD
2h 45mnonstop
JetBlue Logo
6:00 am - 9:17 am
ORD
-
JFK
2h 17mnonstop
$187JetBlue
Tue, Jul 21 - Wed, Jul 22
American Airlines Logo
9:29 pm - 11:30 pm
LGA
-
ORD
3h 01mnonstop
American Airlines Logo
6:30 pm - 9:51 pm
ORD
-
LGA
2h 21mnonstop
$188American Airlines
Wed, Jul 15 - Wed, Jul 22
United Airlines Logo
7:20 am - 9:00 am
LGA
-
ORD
2h 40mnonstop
United Airlines Logo
6:00 am - 9:13 am
ORD
-
LGA
2h 13mnonstop
$192United Airlines
Mon, Sep 14 - Wed, Sep 16
Southwest Logo
2:00 pm - 3:20 pm
LGA
-
MDW
2h 20mnonstop
Southwest Logo
7:50 pm - 10:55 pm
MDW
-
LGA
2h 05mnonstop
$192Southwest
Sat, Sep 19 - Mon, Sep 21
Delta Logo
7:35 pm - 9:37 pm
JFK
-
ORD
3h 02mnonstop
Delta Logo
6:00 am - 9:21 am
ORD
-
JFK
2h 21mnonstop
$192Delta
Sat, Sep 19 - Mon, Sep 21
Delta Logo
6:00 am - 7:32 am
LGA
-
ORD
2h 32mnonstop
Delta Logo
8:12 pm - 11:44 pm
ORD
-
LGA
2h 32mnonstop
$197Delta
Wed, Jul 22 - Fri, Aug 7

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American Airlines flights from Connecticut to Chicago

Our best American Airlines deals on Connecticut to Chicago flight tickets
American Airlines
Aug 22
LGA9:46 pmNew York LaGuardia
2h 56m
ORD11:42 pmChicago O'Hare Intl
Aug 26
ORD3:04 pmChicago O'Hare Intl
2h 18m
LGA6:22 pmNew York LaGuardia
$186
American Airlines
Jul 15
LGA9:29 pmNew York LaGuardia
3h 01m
ORD11:30 pmChicago O'Hare Intl
Jul 22
ORD6:30 pmChicago O'Hare Intl
2h 21m
LGA9:51 pmNew York LaGuardia
$188
American Airlines
Aug 8
LGA6:10 amNew York LaGuardia
2h 49m
ORD7:59 amChicago O'Hare Intl
Aug 10
ORD8:25 pmChicago O'Hare Intl
2h 20m
LGA11:45 pmNew York LaGuardia
$196

United Airlines flights from Connecticut to Chicago

Our best United Airlines deals on Connecticut to Chicago flight tickets
United Airlines
Sep 14
LGA7:20 amNew York LaGuardia
2h 40m
ORD9:00 amChicago O'Hare Intl
Sep 16
ORD6:00 amChicago O'Hare Intl
2h 13m
LGA9:13 amNew York LaGuardia
$192
United Airlines
Aug 10
LGA7:25 pmNew York LaGuardia
2h 47m
ORD9:12 pmChicago O'Hare Intl
Aug 11
ORD8:00 amChicago O'Hare Intl
2h 17m
LGA11:17 amNew York LaGuardia
$195
United Airlines
Aug 4
LGA8:05 amNew York LaGuardia
2h 39m
ORD9:44 amChicago O'Hare Intl
Aug 10
ORD6:29 pmChicago O'Hare Intl
2h 29m
LGA9:58 pmNew York LaGuardia
$200

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 June 21, 2026.
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

Cheapest round-trip

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 8/5

6:59 am-8:47 am

Nonstop2h 48m

Chicago O'Hare Intl

Wed 8/12

6:30 pm-10:06 pm

Nonstop2h 36m

$186

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 8/22

9:46 pm-11:42 pm

Nonstop2h 56m

Chicago O'Hare Intl

Wed 8/26

3:04 pm-6:22 pm

Nonstop2h 18m

$186

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/22

11:20 am-12:57 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sat 7/25

6:00 pm-9:25 pm

Nonstop2h 25m

$187

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 7/22

9:30 pm-11:00 pm

Nonstop2h 30m

Chicago Midway

Sat 7/25

6:40 pm-9:50 pm

Nonstop2h 10m

$187

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 7/21

7:05 am-8:50 am

Nonstop2h 45m

Chicago O'Hare Intl

Wed 7/22

6:00 am-9:17 am

Nonstop2h 17m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/15

9:29 pm-11:30 pm

Nonstop3h 01m

Chicago O'Hare Intl

Wed 7/22

6:30 pm-9:51 pm

Nonstop2h 21m

$188

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 9/14

7:20 am-9:00 am

Nonstop2h 40m

Chicago O'Hare Intl

Wed 9/16

6:00 am-9:13 am

Nonstop2h 13m

$192
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 9/19

2:00 pm-3:20 pm

Nonstop2h 20m

Chicago Midway

Mon 9/21

7:50 pm-10:55 pm

Nonstop2h 05m

$192

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 9/19

7:35 pm-9:37 pm

Nonstop3h 02m

Chicago O'Hare Intl

Mon 9/21

6:00 am-9:21 am

Nonstop2h 21m

$192

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/22

6:00 am-7:32 am

Nonstop2h 32m

Chicago O'Hare Intl

Fri 8/7

8:12 pm-11:44 pm

Nonstop2h 32m

$197

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 November is, on average, the cheapest month to fly to Chicago from Connecticut, with most prices found around $55. If you’re not able to fly to Chicago in November, then January is your next best option. Flight prices from Connecticut to Chicago during January average around $74.

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

$74

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Connecticut in the past 72 hours is $74. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $242.
The fastest flight from Connecticut to Chicago takes 2h 15m
Direct flights go from Connecticut to Chicago every day.
There are 3 airports in Chicago. From Connecticut there are direct flights to Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Connecticut to Chicago

  • 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
7.6
87 reviews
Search Avelo Airlines flights
JetBluePriceFrom $112Free CancellationRating
7.1
2,990 reviews
Search JetBlue flights
DeltaPriceFrom $176Free CancellationRating
7.8
8,423 reviews
Search Delta flights
American AirlinesPriceFrom $177Free CancellationRating
7.1
11,723 reviews
Search American Airlines flights
SouthwestPriceFrom $184Free CancellationRating
7.9
4,244 reviews
Search Southwest flights
United AirlinesPriceFrom $225Free CancellationRating
7.4
9,868 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
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
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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Tue 7/21
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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