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Cheap flights from Connecticut to Chicago from $75

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 5/26. 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.
Multiple Airlines Logo
1:00 pm - 7:41 pm
JFK
-
ORD
7h 41m
1 stop
Multiple Airlines Logo
6:00 am - 9:20 am
ORD
-
JFK
2h 20mnonstop
$159Multiple Airlines
Tue, May 26 - Sat, Jun 13
Frontier Logo
10:00 pm - 7:55 am
LGA
-
ORD
10h 55m
1 stop
Frontier Logo
6:55 am - 5:48 pm
ORD
-
LGA
9h 53m
1 stop
$160Frontier
Tue, May 26 - Tue, Jun 2
JetBlue Logo
7:00 am - 8:45 am
JFK
-
ORD
2h 45mnonstop
JetBlue Logo
6:00 am - 9:20 am
ORD
-
JFK
2h 20mnonstop
$161JetBlue
Mon, Jun 15 - Fri, Jun 19
Frontier Logo
6:29 am - 10:02 pm
LGA
-
MDW
16h 33m
1 stop
Frontier Logo
12:04 pm - 5:53 pm
MDW
-
LGA
28h 49m
1 stop
$162Frontier
Thu, Jun 4 - Mon, Jun 8
Multiple Airlines Logo
1:00 pm - 7:41 pm
JFK
-
ORD
7h 41m
1 stop
Multiple Airlines Logo
3:27 pm - 6:59 pm
ORD
-
JFK
2h 32mnonstop
$164Multiple Airlines
Tue, May 26 - Thu, May 28
Frontier Logo
10:00 pm - 7:55 am
LGA
-
ORD
10h 55m
1 stop
Frontier Logo
1:29 pm - 11:14 pm
ORD
-
LGA
8h 45m
1 stop
$164Frontier
Wed, Jun 3 - Wed, Jun 10
JetBlue Logo
7:00 am - 8:45 am
JFK
-
ORD
2h 45mnonstop
JetBlue Logo
6:00 am - 9:20 am
ORD
-
JFK
2h 20mnonstop
$168JetBlue
Sat, Jun 27 - Sun, Jun 28
Spirit Airlines Logo
6:02 pm - 7:39 pm
LGA
-
ORD
2h 37mnonstop
Spirit Airlines Logo
5:27 pm - 8:41 pm
ORD
-
LGA
2h 14mnonstop
$169Spirit Airlines
Thu, Aug 20 - Sat, Aug 22
United Airlines Logo
6:00 am - 7:42 am
EWR
-
ORD
2h 42mnonstop
United Airlines Logo
6:00 am - 9:12 am
ORD
-
EWR
2h 12mnonstop
$177United Airlines
Tue, Jul 7 - Wed, Jul 15
United Airlines Logo
12:12 pm - 1:57 pm
BDL
-
ORD
2h 45mnonstop
United Airlines Logo
6:30 am - 2:06 pm
ORD
-
BDL
6h 36m
1 stop
$343United Airlines
Tue, Jun 2 - Tue, Jun 9

Delta flights from Connecticut to Chicago

Our best Delta deals on Connecticut to Chicago flight tickets
Delta
Jun 30
JFK7:30 amNew York John F Kennedy Intl
2h 55m
ORD9:25 amChicago O'Hare Intl
Jul 4
ORD6:00 pmChicago O'Hare Intl
2h 40m
JFK9:40 pmNew York John F Kennedy Intl
$177
Delta
Jun 27
LGA5:55 pmNew York LaGuardia
3h 07m
ORD8:02 pmChicago O'Hare Intl
Jun 29
ORD7:05 amChicago O'Hare Intl
2h 19m
LGA10:24 amNew York LaGuardia
$178
Delta
Jul 10
JFK7:35 pmNew York John F Kennedy Intl
3h 17m
ORD9:52 pmChicago O'Hare Intl
Jul 13
ORD6:00 amChicago O'Hare Intl
2h 24m
JFK9:24 amNew York John F Kennedy Intl
$182

United Airlines flights from Connecticut to Chicago

Our best United Airlines deals on Connecticut to Chicago flight tickets
United Airlines
Jul 7
EWR6:00 amNewark
2h 42m
ORD7:42 amChicago O'Hare Intl
Jul 11
ORD6:00 amChicago O'Hare Intl
2h 12m
EWR9:12 amNewark
$177
United Airlines
Jun 17
LGA6:00 amNew York LaGuardia
2h 39m
ORD7:39 amChicago O'Hare Intl
Jun 19
ORD6:25 pmChicago O'Hare Intl
2h 29m
LGA9:54 pmNew York LaGuardia
$182
United Airlines
May 27
EWR6:00 amNewark
2h 42m
ORD7:42 amChicago O'Hare Intl
May 28
ORD6:00 amChicago O'Hare Intl
2h 12m
EWR9:12 amNewark
$187

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 May 7, 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

Tue 5/26

1:00 pm-7:41 pm

1 stop7h 41m

Chicago O'Hare Intl

Sat 6/13

6:00 am-9:20 am

Nonstop2h 20m

$159

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 5/26

10:00 pm-7:55 am

1 stop10h 55m

Chicago O'Hare Intl

Tue 6/2

6:55 am-5:48 pm

1 stop9h 53m

$160

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 6/15

7:00 am-8:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Fri 6/19

6:00 am-9:20 am

Nonstop2h 20m

$161

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 6/4

6:29 am-10:02 pm

1 stop16h 33m

Chicago Midway

Mon 6/8

12:04 pm-5:53 pm

1 stop28h 49m

$162

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 5/26

1:00 pm-7:41 pm

1 stop7h 41m

Chicago O'Hare Intl

Thu 5/28

3:27 pm-6:59 pm

Nonstop2h 32m

$164

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 6/3

10:00 pm-7:55 am

1 stop10h 55m

Chicago O'Hare Intl

Wed 6/10

1:29 pm-11:14 pm

1 stop8h 45m

$164

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 6/27

7:00 am-8:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Sun 6/28

6:00 am-9:20 am

Nonstop2h 20m

$168
Quickest round-trip

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 8/20

6:02 pm-7:39 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sat 8/22

5:27 pm-8:41 pm

Nonstop2h 14m

$169

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 7/7

6:00 am-7:42 am

Nonstop2h 42m

Chicago O'Hare Intl

Wed 7/15

6:00 am-9:12 am

Nonstop2h 12m

$177

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 6/2

12:12 pm-1:57 pm

Nonstop2h 45m

Chicago O'Hare Intl

Tue 6/9

6:30 am-2:06 pm

1 stop6h 36m

$343

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 $51. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from Connecticut to Chicago during November average around $55.

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

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

$132

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 $132. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $142.
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
88 reviews
Search Avelo Airlines flights
American AirlinesPriceFrom $157Free CancellationRating
7.1
11,669 reviews
Search American Airlines flights
DeltaPriceFrom $176Free CancellationRating
7.9
8,459 reviews
Search Delta flights
SouthwestPriceFrom $184Free CancellationRating
7.9
4,301 reviews
Search Southwest flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,692 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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