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Cheap flights from Connecticut to Chicago from $105

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 9/8. 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.
Multiple Airlines Logo
1:00 pm - 6:23 pmJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
6h 23m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
10:59 am - 2:20 pmORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 21mnonstop
$213Multiple Airlines
Sat, Sep 12 - Fri, Sep 25
JetBlue Logo
8:00 pm - 9:58 pmJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
2h 58mnonstop
JetBlue Logo
5:27 pm - 9:00 pmORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 33mnonstop
$217JetBlue
Wed, Sep 2 - Sat, Sep 5
American Airlines Logo
8:27 am - 10:30 amJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
3h 03mnonstop
American Airlines Logo
4:30 pm - 8:01 pmORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 31mnonstop
$217American Airlines
Wed, Aug 26 - Sat, Aug 29
American Airlines Logo
2:59 pm - 4:58 pmJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
American Airlines Logo
4:30 pm - 8:01 pmORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 31mnonstop
$217American Airlines
Tue, Aug 25 - Sat, Aug 29
Frontier Logo
11:35 am - 6:23 pmEWR  Newark-ORD Chicago O'Hare Intl
7h 48m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:50 pm - 1:01 amORD  Chicago O'Hare Intl-EWR Newark
8h 11m1 stop Orlando
$217Frontier
Mon, Oct 5 - Tue, Oct 6
Frontier Logo
11:30 am - 11:08 pmEWR  Newark-ORD Chicago O'Hare Intl
12h 38m1 stop Orlando
Frontier Logo
3:50 pm - 1:01 amORD  Chicago O'Hare Intl-EWR Newark
8h 11m1 stop Orlando
$217Frontier
Sat, Sep 5 - Tue, Sep 29
JetBlue Logo
8:00 pm - 9:58 pmJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
2h 58mnonstop
JetBlue Logo
5:27 pm - 9:00 pmORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 33mnonstop
$217JetBlue
Wed, Sep 2 - Sat, Sep 5
Multiple Airlines Logo
3:38 pm - 11:08 pmEWR  Newark-ORD Chicago O'Hare Intl
8h 30m1 stop Fort Lauderdale
Multiple Airlines Logo
3:50 pm - 1:01 amORD  Chicago O'Hare Intl-EWR Newark
8h 11m1 stop Orlando
$220Multiple Airlines
Fri, Oct 2 - Mon, Oct 5
United Airlines Logo
7:45 am - 1:04 pmEWR  Newark-ORD Chicago O'Hare Intl
6h 19m1 stop Cleveland Hopkins Intl
United Airlines Logo
12:55 pm - 5:39 pmORD  Chicago O'Hare Intl-EWR Newark
3h 44m1 stop Cleveland Hopkins Intl
$224United Airlines
Sun, Nov 1 - Wed, Nov 4
United Airlines Logo
7:20 am - 9:00 amLGA  New York LaGuardia-ORD Chicago O'Hare Intl
2h 40mnonstop
United Airlines Logo
6:00 pm - 9:25 pmORD  Chicago O'Hare Intl-LGA New York LaGuardia
2h 25mnonstop
$227United Airlines
Wed, Sep 2 - Wed, Sep 2

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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 25
JFK2:59 pmNew York John F Kennedy Intl
2h 59m
ORD4:58 pmChicago O'Hare Intl
Aug 29
ORD4:30 pmChicago O'Hare Intl
2h 31m
JFK8:01 pmNew York John F Kennedy Intl
$217
American Airlines
Sep 1
LGA4:00 pmNew York LaGuardia
2h 57m
ORD5:57 pmChicago O'Hare Intl
Sep 2
ORD8:00 amChicago O'Hare Intl
2h 16m
LGA11:16 amNew York LaGuardia
$218
American Airlines
Sep 2
EWR6:50 amNewark
2h 46m
ORD8:36 amChicago O'Hare Intl
Sep 2
ORD5:49 pmChicago O'Hare Intl
2h 25m
EWR9:14 pmNewark
$219

Delta flights from Connecticut to Chicago

Our best Delta deals on Connecticut to Chicago flight tickets
Delta
Aug 26
JFK7:35 pmNew York John F Kennedy Intl
3h 17m
ORD9:52 pmChicago O'Hare Intl
Aug 29
ORD6:00 pmChicago O'Hare Intl
2h 37m
JFK9:37 pmNew York John F Kennedy Intl
$227
Delta
Sep 8
JFK7:35 pmNew York John F Kennedy Intl
3h 02m
ORD9:37 pmChicago O'Hare Intl
Sep 9
ORD6:00 amChicago O'Hare Intl
2h 21m
JFK9:21 amNew York John F Kennedy Intl
$232
Delta
Aug 11
JFK3:00 pmNew York John F Kennedy Intl
3h 06m
ORD5:06 pmChicago O'Hare Intl
Aug 18
ORD1:00 pmChicago O'Hare Intl
2h 33m
JFK4:33 pmNew York John F Kennedy Intl
$235

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 August 9, 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 New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Sat 9/12

1:00 pm-6:23 pm

1 stop6h 23m

Chicago O'Hare Intl

Fri 9/25

10:59 am-2:20 pm

Nonstop2h 21m

$213

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Wed 9/2

8:00 pm-9:58 pm

Nonstop2h 58m

Chicago O'Hare Intl

Sat 9/5

5:27 pm-9:00 pm

Nonstop2h 33m

$217

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Wed 8/26

8:27 am-10:30 am

Nonstop3h 03m

Chicago O'Hare Intl

Sat 8/29

4:30 pm-8:01 pm

Nonstop2h 31m

$217

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Tue 8/25

2:59 pm-4:58 pm

Nonstop2h 59m

Chicago O'Hare Intl

Sat 8/29

4:30 pm-8:01 pm

Nonstop2h 31m

$217

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Mon 10/5

11:35 am-6:23 pm

1 stop7h 48m

Chicago O'Hare Intl

Tue 10/6

3:50 pm-1:01 am

1 stop8h 11m

$217

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Sat 9/5

11:30 am-11:08 pm

1 stop12h 38m

Chicago O'Hare Intl

Tue 9/29

3:50 pm-1:01 am

1 stop8h 11m

$217

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Wed 9/2

8:00 pm-9:58 pm

Nonstop2h 58m

Chicago O'Hare Intl

Sat 9/5

5:27 pm-9:00 pm

Nonstop2h 33m

$217

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Fri 10/2

3:38 pm-11:08 pm

1 stop8h 30m

Chicago O'Hare Intl

Mon 10/5

3:50 pm-1:01 am

1 stop8h 11m

$220

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Sun 11/1

7:45 am-1:04 pm

1 stop6h 19m

Chicago O'Hare Intl

Wed 11/4

12:55 pm-5:39 pm

1 stop3h 44m

$224
Quickest round-trip

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Wed 9/2

7:20 am-9:00 am

Nonstop2h 40m

Chicago O'Hare Intl

Wed 9/2

6:00 pm-9:25 pm

Nonstop2h 25m

$227

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 January is, on average, the cheapest month to fly to Chicago from Connecticut, with most prices found around $330. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Connecticut to Chicago during September average around $338.

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

$59

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 $59. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $161.
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
7.5
85 reviews
Search Avelo Airlines flights
JetBluePriceFrom $84Free CancellationRating
7.1
3,030 reviews
Search JetBlue flights
DeltaPriceFrom $176Free CancellationRating
7.8
8,500 reviews
Search Delta flights
American AirlinesPriceFrom $216Free CancellationRating
7.1
11,894 reviews
Search American Airlines flights
United AirlinesPriceFrom $234Free CancellationRating
7.4
10,089 reviews
Search United Airlines flights
SouthwestPriceFrom $279Free CancellationRating
8.0
4,216 reviews
Search Southwest flights

Traveling to a place near Chicago?

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