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Cheap flights from Connecticut to Chicago from $51

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 3/10. 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.
Frontier Logo
4:29 pm - 6:29 pm
JFK
-
ORD
3h 00mnonstop
Frontier Logo
11:55 am - 3:19 pm
ORD
-
JFK
2h 24mnonstop
$83Frontier
jue., feb. 5 - dom., feb. 8
Spirit Airlines Logo
8:37 pm - 10:07 pm
LGA
-
ORD
2h 30mnonstop
Spirit Airlines Logo
5:53 pm - 8:59 pm
ORD
-
LGA
2h 06mnonstop
$83Spirit Airlines
mar., ene. 6 - dom., ene. 11
Multiple Airlines Logo
7:55 am - 7:44 pm
EWR
-
ORD
12h 49m1 stop
Multiple Airlines Logo
4:38 pm - 7:46 pm
ORD
-
EWR
2h 08mnonstop
$108Multiple Airlines
sáb., ene. 24 - lun., ene. 26
Multiple Airlines Logo
9:05 pm - 10:42 pm
EWR
-
ORD
2h 37mnonstop
Multiple Airlines Logo
2:42 pm - 1:08 am
ORD
-
EWR
9h 26m1 stop
$114Multiple Airlines
dom., ene. 25 - dom., feb. 1
Southwest Logo
9:00 am - 10:40 am
LGA
-
MDW
2h 40mnonstop
Southwest Logo
7:15 pm - 10:20 pm
MDW
-
LGA
2h 05mnonstop
$139Southwest
jue., ene. 15 - dom., ene. 18
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
Southwest Logo
5:55 pm - 9:00 pm
MDW
-
LGA
2h 05mnonstop
$149Southwest
jue., ene. 8 - lun., ene. 12
United Airlines Logo
6:00 am - 9:43 am
BDL
-
ORD
4h 43m1 stop
United Airlines Logo
11:04 am - 2:22 pm
ORD
-
BDL
2h 18mnonstop
$167United Airlines
sáb., ene. 17 - dom., ene. 18
United Airlines Logo
6:15 am - 8:05 am
BDL
-
ORD
2h 50mnonstop
United Airlines Logo
7:10 am - 10:36 am
ORD
-
BDL
2h 26mnonstop
$175United Airlines
jue., dic. 25 - jue., ene. 1
Delta Logo
12:48 pm - 5:26 pm
BDL
-
MDW
5h 38m1 stop
Delta Logo
6:08 pm - 11:14 pm
MDW
-
BDL
4h 06m1 stop
$177Delta
mié., dic. 24 - mié., dic. 31
Delta Logo
5:30 am - 9:01 am
BDL
-
ORD
4h 31m1 stop
Delta Logo
6:02 pm - 11:14 pm
ORD
-
BDL
4h 12m1 stop
$177Delta
jue., dic. 25 - mié., dic. 31

Frontier flights from Connecticut to Chicago

Our best Frontier deals on Connecticut to Chicago flight tickets
Frontier
Feb 20
JFK11:03 amNew York John F Kennedy Intl
3h 00m
ORD1:03 pmChicago O'Hare Intl
Feb 22
ORD6:40 amChicago O'Hare Intl
2h 24m
JFK10:04 amNew York John F Kennedy Intl
$83
Find similar
Frontier
Jan 30
JFK4:29 pmNew York John F Kennedy Intl
3h 00m
ORD6:29 pmChicago O'Hare Intl
Feb 1
ORD11:55 amChicago O'Hare Intl
2h 24m
JFK3:19 pmNew York John F Kennedy Intl
$84
Find similar
Frontier
Feb 19
JFK11:00 amNew York John F Kennedy Intl
2h 57m
ORD12:57 pmChicago O'Hare Intl
Feb 22
ORD6:40 amChicago O'Hare Intl
2h 24m
JFK10:04 amNew York John F Kennedy Intl
$85
Find similar

American Airlines flights from Connecticut to Chicago

Our best American Airlines deals on Connecticut to Chicago flight tickets
American Airlines
Jan 15
EWR7:00 amNewark
2h 53m
ORD8:53 amChicago O'Hare Intl
Jan 18
ORD7:49 pmChicago O'Hare Intl
2h 10m
EWR10:59 pmNewark
$154
Find similar
American Airlines
Dec 17
JFK9:00 amNew York John F Kennedy Intl
2h 49m
ORD10:49 amChicago O'Hare Intl
Dec 17
ORD4:04 pmChicago O'Hare Intl
2h 25m
JFK7:29 pmNew York John F Kennedy Intl
$164
Find similar
American Airlines
Dec 17
JFK9:00 amNew York John F Kennedy Intl
2h 49m
ORD10:49 amChicago O'Hare Intl
Dec 25
ORD1:51 pmChicago O'Hare Intl
4h 58m
1 stop
JFK7:49 pmNew York John F Kennedy Intl
$242
Find similar

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 diciembre 11, 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

jue. 2/5

4:29 pm-6:29 pm

Nonstop3h 00m

Chicago O'Hare Intl

dom. 2/8

11:55 am-3:19 pm

Nonstop2h 24m

$83

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mar. 1/6

8:37 pm-10:07 pm

Nonstop2h 30m

Chicago O'Hare Intl

dom. 1/11

5:53 pm-8:59 pm

Nonstop2h 06m

$83

NewarkChicago

EWR - ORD

EWRORD

Newark

sáb. 1/24

7:55 am-7:44 pm

1 stop12h 49m

Chicago O'Hare Intl

lun. 1/26

4:38 pm-7:46 pm

Nonstop2h 08m

$108

NewarkChicago

EWR - ORD

EWRORD

Newark

dom. 1/25

9:05 pm-10:42 pm

Nonstop2h 37m

Chicago O'Hare Intl

dom. 2/1

2:42 pm-1:08 am

1 stop9h 26m

$114

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 1/15

9:00 am-10:40 am

Nonstop2h 40m

Chicago Midway

dom. 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 1/8

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

lun. 1/12

5:55 pm-9:00 pm

Nonstop2h 05m

$149

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

sáb. 1/17

6:00 am-9:43 am

1 stop4h 43m

Chicago O'Hare Intl

dom. 1/18

11:04 am-2:22 pm

Nonstop2h 18m

$167

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

jue. 12/25

6:15 am-8:05 am

Nonstop2h 50m

Chicago O'Hare Intl

jue. 1/1

7:10 am-10:36 am

Nonstop2h 26m

$175

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

mié. 12/24

12:48 pm-5:26 pm

1 stop5h 38m

Chicago Midway

mié. 12/31

6:08 pm-11:14 pm

1 stop4h 06m

$177

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

jue. 12/25

5:30 am-9:01 am

1 stop4h 31m

Chicago O'Hare Intl

mié. 12/31

6:02 pm-11:14 pm

1 stop4h 12m

$177

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 October is, on average, the cheapest month to fly to Chicago from Connecticut, with most prices found around $296. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Connecticut to Chicago during September average around $301.

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

$50

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Connecticut in the past 72 hours is $50. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $98.
The fastest flight from Connecticut to Chicago takes 2h 20m
Direct flights go from Connecticut to Chicago every day.
There are 3 airports in Chicago. From Connecticut there are direct flights to Chicago O'Hare Intl (ORD), 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
FrontierPriceFrom $97Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
Avelo AirlinesPriceFrom $104Free CancellationRating
7.5
84 reviews
Search Avelo Airlines flights
DeltaPriceFrom $176Free CancellationRating
7.9
8,007 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
7.9
4,253 reviews
Search Southwest flights
American AirlinesPriceFrom $178Free CancellationRating
7.2
11,049 reviews
Search American Airlines flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
9,094 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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sáb. 1/10
sáb. 1/17
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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