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Cheap flights from Connecticut to Chicago from $27

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 9/6. 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

Spirit Airlines Logo
3:13 pm - 4:51 pmLGA-ORD
2h 38mnonstop
Spirit Airlines Logo
11:57 am - 11:25 pmORD-LGA
10h 28m1 stop
$66Spirit Airlines
Find Deal
mié., sep. 10 - sáb., sep. 13
Spirit Airlines Logo
6:30 am - 4:12 pmLGA-ORD
10h 42m1 stop
Spirit Airlines Logo
4:35 pm - 7:41 pmORD-LGA
2h 06mnonstop
$68Spirit Airlines
Find Deal
mar., sep. 9 - sáb., sep. 13
Frontier Logo
11:00 am - 12:45 pmJFK-ORD
2h 45mnonstop
Frontier Logo
6:40 am - 10:03 amORD-JFK
2h 23mnonstop
$104Frontier
Find Deal
sáb., nov. 8 - lun., nov. 10
Frontier Logo
11:00 am - 12:45 pmJFK-ORD
2h 45mnonstop
Frontier Logo
6:40 am - 10:03 amORD-JFK
2h 23mnonstop
$105Frontier
Find Deal
sáb., oct. 18 - mié., oct. 22
United Airlines Logo
7:00 am - 8:38 amEWR-ORD
2h 38mnonstop
United Airlines Logo
7:10 am - 10:28 amORD-EWR
2h 18mnonstop
$117United Airlines
Find Deal
mié., sep. 3 - mié., sep. 10
American Airlines Logo
7:22 pm - 9:01 pmEWR-ORD
2h 39mnonstop
American Airlines Logo
3:42 pm - 6:59 pmORD-EWR
2h 17mnonstop
$118American Airlines
Find Deal
sáb., sep. 20 - sáb., sep. 27
American Airlines Logo
7:19 am - 9:05 amEWR-ORD
2h 46mnonstop
American Airlines Logo
5:35 pm - 8:45 pmORD-EWR
2h 10mnonstop
$119American Airlines
Find Deal
mar., ene. 6 - mié., ene. 7
United Airlines Logo
9:44 pm - 11:25 pmEWR-ORD
2h 41mnonstop
United Airlines Logo
9:08 pm - 12:30 amORD-EWR
2h 22mnonstop
$121United Airlines
Find Deal
vie., sep. 5 - lun., sep. 8
JetBlue Logo
8:30 pm - 10:28 pmJFK-ORD
2h 58mnonstop
JetBlue Logo
1:37 pm - 4:59 pmORD-JFK
2h 22mnonstop
$123JetBlue
Find Deal
mar., sep. 2 - mar., sep. 9
JetBlue Logo
8:30 pm - 10:28 pmJFK-ORD
2h 58mnonstop
JetBlue Logo
1:37 pm - 4:59 pmORD-JFK
2h 22mnonstop
$127JetBlue
Find Deal
mar., sep. 2 - mar., sep. 9

JetBlue flights from Connecticut to Chicago O'Hare Intl Airport

Our best JetBlue deals on Connecticut to Chicago O'Hare Intl Airport flight tickets
JetBlue
Sep 2
JFK8:30 pmNew York John F Kennedy Intl
2h 58m
ORD10:28 pmChicago O'Hare Intl
Sep 9
ORD1:37 pmChicago O'Hare Intl
2h 22m
JFK4:59 pmNew York John F Kennedy Intl
$123
Find similar
JetBlue
Sep 2
JFK8:30 pmNew York John F Kennedy Intl
2h 58m
ORD10:28 pmChicago O'Hare Intl
Sep 9
ORD1:37 pmChicago O'Hare Intl
2h 22m
JFK4:59 pmNew York John F Kennedy Intl
$127
Find similar
JetBlue
Sep 2
JFK8:30 pmNew York John F Kennedy Intl
2h 58m
ORD10:28 pmChicago O'Hare Intl
Sep 3
ORD6:10 amChicago O'Hare Intl
2h 19m
JFK9:29 amNew York John F Kennedy Intl
$137
Find similar

Avelo Airlines flights from Connecticut to Chicago O'Hare Intl Airport

Our best Avelo Airlines deals on Connecticut to Chicago O'Hare Intl Airport flight tickets
Avelo Airlines
Aug 28
HVN1:45 pmTweed-New Haven
2h 20m
ORD3:05 pmChicago O'Hare Intl
Sep 4
ORD6:02 pmChicago O'Hare Intl
2h 08m
HVN9:10 pmTweed-New Haven
$143
Find similar
Avelo Airlines
Aug 28
HVN1:45 pmTweed-New Haven
2h 20m
ORD3:05 pmChicago O'Hare Intl
Aug 31
ORD3:55 pmChicago O'Hare Intl
2h 10m
HVN7:05 pmTweed-New Haven
$148
Find similar
Avelo Airlines
Sep 11
HVN3:50 pmTweed-New Haven
2h 21m
ORD5:11 pmChicago O'Hare Intl
Sep 14
ORD6:02 pmChicago O'Hare Intl
2h 08m
HVN9:10 pmTweed-New Haven
$168
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Connecticut to Chicago O'Hare Intl Airport 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 agosto 6, 2025.
Use the filters below to find and compare flights from Connecticut to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 9/10

3:13 pm-4:51 pm

Nonstop2h 38m

Chicago O'Hare Intl

sáb. 9/13

11:57 am-11:25 pm

1 stop10h 28m

$66

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mar. 9/9

6:30 am-4:12 pm

1 stop10h 42m

Chicago O'Hare Intl

sáb. 9/13

4:35 pm-7:41 pm

Nonstop2h 06m

$68

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

sáb. 11/8

11:00 am-12:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

lun. 11/10

6:40 am-10:03 am

Nonstop2h 23m

$104

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

sáb. 10/18

11:00 am-12:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

mié. 10/22

6:40 am-10:03 am

Nonstop2h 23m

$105

NewarkChicago

EWR - ORD

EWRORD

Newark

mié. 9/3

7:00 am-8:38 am

Nonstop2h 38m

Chicago O'Hare Intl

mié. 9/10

7:10 am-10:28 am

Nonstop2h 18m

$117

NewarkChicago

EWR - ORD

EWRORD

Newark

sáb. 9/20

7:22 pm-9:01 pm

Nonstop2h 39m

Chicago O'Hare Intl

sáb. 9/27

3:42 pm-6:59 pm

Nonstop2h 17m

$118

NewarkChicago

EWR - ORD

EWRORD

Newark

mar. 1/6

7:19 am-9:05 am

Nonstop2h 46m

Chicago O'Hare Intl

mié. 1/7

5:35 pm-8:45 pm

Nonstop2h 10m

$119

NewarkChicago

EWR - ORD

EWRORD

Newark

vie. 9/5

9:44 pm-11:25 pm

Nonstop2h 41m

Chicago O'Hare Intl

lun. 9/8

9:08 pm-12:30 am

Nonstop2h 22m

$121

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mar. 9/2

8:30 pm-10:28 pm

Nonstop2h 58m

Chicago O'Hare Intl

mar. 9/9

1:37 pm-4:59 pm

Nonstop2h 22m

$123

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mar. 9/2

8:30 pm-10:28 pm

Nonstop2h 58m

Chicago O'Hare Intl

mar. 9/9

1:37 pm-4:59 pm

Nonstop2h 22m

$127

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Connecticut averaging around $323.

What is the cheapest Connecticut to Chicago O'Hare Intl flight route?

Fly from Tweed-New Haven to Chicago O'Hare Intl for the best Connecticut - Chicago O'Hare Intl flight prices

What cabin class options are available on Connecticut to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Connecticut to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Connecticut to Chicago O'Hare Intl Airport.

Cheap Connecticut to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Connecticut to Chicago O'Hare Intl Airport

Best Price Found

$27

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Connecticut in the past 72 hours is $27. The best round-trip flight deal from Connecticut to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $66.
The fastest flight from Connecticut to Chicago O'Hare Intl Airport takes 2h 20m
Direct flights go from Connecticut to Chicago O'Hare Intl Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Connecticut to Chicago O'Hare Intl Airport?

    Prices for flights from Connecticut to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Connecticut to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Connecticut to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Connecticut to Chicago O'Hare Intl Airport?

Best airlines flying from Connecticut to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Connecticut to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $116Free CancellationRating
5.8
3,231 reviews
Search Frontier flights
American AirlinesPriceFrom $181Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $202Free CancellationRating
6.3
8,055 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,917 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Orland Park
Aurora
Janesville
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Connecticut to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Connecticut to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Connecticut to Chicago with flexible booking policies on momondo?

Flights from Connecticut to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Connecticut to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Connecticut.

I’m not ready to book a flight from Connecticut to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Connecticut to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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