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Cheap flights from Connecticut to Chicago from $58

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 5/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
6:30 am - 8:01 am
LGA
-
ORD
2h 31mnonstop
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
$102Spirit Airlines
seg, abr 13 - sex, abr 17
Spirit Airlines Logo
2:38 pm - 4:14 pm
LGA
-
ORD
2h 36mnonstop
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
$103Spirit Airlines
sáb, abr 18 - seg, abr 20
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$113Frontier
sex, abr 24 - dom, abr 26
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$115Frontier
qui, abr 30 - dom, mai 3
Multiple Airlines Logo
10:54 pm - 12:22 am
EWR
-
ORD
2h 28mnonstop
Multiple Airlines Logo
6:08 pm - 1:16 am
ORD
-
EWR
6h 08m
1 stop
$121Multiple Airlines
qua, abr 8 - qua, abr 29
Multiple Airlines Logo
1:00 pm - 7:51 pm
JFK
-
ORD
7h 51m
1 stop
Multiple Airlines Logo
8:35 am - 12:00 pm
ORD
-
JFK
2h 25mnonstop
$150Multiple Airlines
ter, mai 5 - qua, mai 13
JetBlue Logo
6:00 am - 7:41 am
JFK
-
ORD
2h 41mnonstop
JetBlue Logo
8:34 am - 11:59 am
ORD
-
JFK
2h 25mnonstop
$154JetBlue
ter, mai 5 - qua, mai 6
JetBlue Logo
6:00 am - 7:44 am
JFK
-
ORD
2h 44mnonstop
JetBlue Logo
8:35 am - 12:00 pm
ORD
-
JFK
2h 25mnonstop
$157JetBlue
ter, mai 12 - ter, mai 19
Delta Logo
10:24 am - 12:26 pm
JFK
-
ORD
3h 02mnonstop
Delta Logo
6:21 pm - 9:57 pm
ORD
-
JFK
2h 36mnonstop
$159Delta
ter, abr 21 - ter, abr 21
Delta Logo
7:36 pm - 9:57 pm
JFK
-
ORD
3h 21mnonstop
Delta Logo
6:04 am - 9:29 am
ORD
-
JFK
2h 25mnonstop
$160Delta
sáb, abr 18 - ter, abr 21

American Airlines flights from Connecticut to Chicago

Our best American Airlines deals on Connecticut to Chicago flight tickets
American Airlines
May 16
JFK9:03 amNew York John F Kennedy Intl
2h 55m
ORD10:58 amChicago O'Hare Intl
May 23
ORD3:24 pmChicago O'Hare Intl
2h 35m
JFK6:59 pmNew York John F Kennedy Intl
$200
American Airlines
Apr 4
JFK12:59 pmNew York John F Kennedy Intl
8h 01m
1 stop
ORD8:00 pmChicago O'Hare Intl
Apr 7
ORD11:22 amChicago O'Hare Intl
2h 29m
JFK2:51 pmNew York John F Kennedy Intl
$237
American Airlines
Apr 4
JFK12:59 pmNew York John F Kennedy Intl
8h 01m
1 stop
ORD8:00 pmChicago O'Hare Intl
Apr 6
ORD7:52 amChicago O'Hare Intl
2h 26m
JFK11:18 amNew York John F Kennedy Intl
$239

Spirit Airlines flights from Connecticut to Chicago

Our best Spirit Airlines deals on Connecticut to Chicago flight tickets
Spirit Airlines
Apr 13
LGA6:30 amNew York LaGuardia
2h 31m
ORD8:01 amChicago O'Hare Intl
Apr 16
ORD2:09 pmChicago O'Hare Intl
2h 11m
LGA5:20 pmNew York LaGuardia
$102
Spirit Airlines
Apr 18
LGA2:38 pmNew York LaGuardia
2h 36m
ORD4:14 pmChicago O'Hare Intl
Apr 20
ORD2:09 pmChicago O'Hare Intl
2h 11m
LGA5:20 pmNew York LaGuardia
$103
Spirit Airlines
Apr 13
LGA6:30 amNew York LaGuardia
2h 31m
ORD8:01 amChicago O'Hare Intl
Apr 21
ORD2:09 pmChicago O'Hare Intl
2h 11m
LGA5:20 pmNew York LaGuardia
$105

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 março 26, 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

LGA - ORD

LGAORD

New York LaGuardia

seg 4/13

6:30 am-8:01 am

Nonstop2h 31m

Chicago O'Hare Intl

sex 4/17

2:09 pm-5:20 pm

Nonstop2h 11m

$102

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb 4/18

2:38 pm-4:14 pm

Nonstop2h 36m

Chicago O'Hare Intl

seg 4/20

2:09 pm-5:20 pm

Nonstop2h 11m

$103
Quickest round-trip

NewarkChicago

EWR - MDW

EWRMDW

Newark

sex 4/24

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

dom 4/26

7:30 am-10:38 am

Nonstop2h 08m

$113

NewarkChicago

EWR - MDW

EWRMDW

Newark

qui 4/30

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

dom 5/3

7:30 am-10:38 am

Nonstop2h 08m

$115

NewarkChicago

EWR - ORD

EWRORD

Newark

qua 4/8

10:54 pm-12:22 am

Nonstop2h 28m

Chicago O'Hare Intl

qua 4/29

6:08 pm-1:16 am

1 stop6h 08m

$121

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

ter 5/5

1:00 pm-7:51 pm

1 stop7h 51m

Chicago O'Hare Intl

qua 5/13

8:35 am-12:00 pm

Nonstop2h 25m

$150

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

ter 5/5

6:00 am-7:41 am

Nonstop2h 41m

Chicago O'Hare Intl

qua 5/6

8:34 am-11:59 am

Nonstop2h 25m

$154

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

ter 5/12

6:00 am-7:44 am

Nonstop2h 44m

Chicago O'Hare Intl

ter 5/19

8:35 am-12:00 pm

Nonstop2h 25m

$157

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

ter 4/21

10:24 am-12:26 pm

Nonstop3h 02m

Chicago O'Hare Intl

ter 4/21

6:21 pm-9:57 pm

Nonstop2h 36m

$159

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

sáb 4/18

7:36 pm-9:57 pm

Nonstop3h 21m

Chicago O'Hare Intl

ter 4/21

6:04 am-9:29 am

Nonstop2h 25m

$160

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 $288. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from Connecticut to Chicago during October average around $300.

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

$206

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 $206. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $165.
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

  • 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 $76Free CancellationRating
7.6
88 reviews
Search Avelo Airlines flights
American AirlinesPriceFrom $170Free CancellationRating
7.1
11,494 reviews
Search American Airlines flights
DeltaPriceFrom $176Free CancellationRating
7.9
8,326 reviews
Search Delta flights
SouthwestPriceFrom $184Free CancellationRating
8.0
4,333 reviews
Search Southwest flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
9,482 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
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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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