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Cheap flights from Connecticut to Chicago from $62

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.
Avelo Airlines Logo
4:34 pm - 6:27 pmHVN  Tweed-New Haven-ORD Chicago O'Hare Intl
2h 53mnonstop
Avelo Airlines Logo
7:21 pm - 10:39 pmORD  Chicago O'Hare Intl-HVN Tweed-New Haven
2h 18mnonstop
$206Avelo Airlines
Thu, Feb 18 - Sun, Feb 21
Avelo Airlines Logo
4:20 pm - 6:13 pmHVN  Tweed-New Haven-ORD Chicago O'Hare Intl
2h 53mnonstop
Avelo Airlines Logo
7:08 pm - 10:31 pmORD  Chicago O'Hare Intl-HVN Tweed-New Haven
2h 23mnonstop
$214Avelo Airlines
Tue, Dec 29 - Thu, Dec 31
Multiple Airlines Logo
6:44 pm - 2:30 pmHVN  Tweed-New Haven-ORD Chicago O'Hare Intl
20h 46m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
Multiple Airlines Logo
3:30 pm - 7:04 pmORD  Chicago O'Hare Intl-HVN Tweed-New Haven
26h 34m1 stop Fort Myers SW Florida Intl
$298Multiple Airlines
Mon, Dec 7 - Thu, Dec 10
Multiple Airlines Logo
6:30 am - 9:29 pmHVN  Tweed-New Haven-ORD Chicago O'Hare Intl
15h 59m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
7:07 pm - 10:30 pmORD  Chicago O'Hare Intl-HVN Tweed-New Haven
2h 23mnonstop
$299Multiple Airlines
Fri, Dec 11 - Sun, Dec 13
United Airlines Logo
6:00 am - 11:32 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
6h 32m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
6:15 pm - 9:37 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 22mnonstop
$303United Airlines
Thu, Jan 7 - Sat, Jan 9
United Airlines Logo
6:00 am - 11:33 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
6h 33m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
10:57 am - 2:15 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 18mnonstop
$303United Airlines
Mon, Dec 14 - Wed, Dec 16
American Airlines Logo
5:15 am - 11:34 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
7h 19m1 stop Washington, D.C. Reagan-National
American Airlines Logo
8:30 pm - 11:52 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 22mnonstop
$307American Airlines
Mon, Dec 14 - Mon, Dec 14
American Airlines Logo
5:30 am - 11:44 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
7h 14m1 stop Washington, D.C. Reagan-National
American Airlines Logo
8:10 am - 11:23 amORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 13mnonstop
$307American Airlines
Tue, Dec 1 - Mon, Dec 7
JetBlue Logo
12:00 pm - 11:33 pmBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
12h 33m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 11:59 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
8h 00m1 stop Fort Lauderdale
$309JetBlue
Fri, Dec 4 - Sat, Dec 5
JetBlue Logo
12:00 pm - 11:33 pmBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
12h 33m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 11:59 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
8h 00m1 stop Fort Lauderdale
$309JetBlue
Wed, Dec 2 - Sat, Dec 5

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

Our best American Airlines deals on Connecticut to Chicago O'Hare Intl Airport flight tickets
American Airlines
Dec 5
BDL12:17 pmHartford Bradley Intl
2h 53m
ORD2:10 pmChicago O'Hare Intl
Dec 12
ORD8:10 amChicago O'Hare Intl
2h 13m
BDL11:23 amHartford Bradley Intl
$321
American Airlines
Dec 4
BDL6:17 pmHartford Bradley Intl
3h 07m
ORD8:24 pmChicago O'Hare Intl
Dec 6
ORD8:30 pmChicago O'Hare Intl
2h 22m
BDL11:52 pmHartford Bradley Intl
$362
American Airlines
Dec 3
BDL6:17 pmHartford Bradley Intl
3h 07m
ORD8:24 pmChicago O'Hare Intl
Dec 6
ORD6:59 amChicago O'Hare Intl
6h 21m
1 stop
BDL2:20 pmHartford Bradley Intl
$367

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
Feb 18
HVN4:34 pmTweed-New Haven
2h 53m
ORD6:27 pmChicago O'Hare Intl
Feb 21
ORD7:21 pmChicago O'Hare Intl
2h 18m
HVN10:39 pmTweed-New Haven
$206
Avelo Airlines
Nov 15
HVN4:45 pmTweed-New Haven
2h 39m
ORD6:24 pmChicago O'Hare Intl
Nov 19
ORD7:13 pmChicago O'Hare Intl
2h 23m
HVN10:36 pmTweed-New Haven
$214
Avelo Airlines
Nov 22
HVN4:35 pmTweed-New Haven
2h 53m
ORD6:28 pmChicago O'Hare Intl
Nov 26
ORD7:00 pmChicago O'Hare Intl
2h 23m
HVN10:23 pmTweed-New Haven
$233

momondo Fare Finder

 
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

Cheapest round-trip
Quickest round-trip

New HavenChicago

HVN Tweed-New Haven - ORD Chicago O'Hare Intl

HVNORD

Tweed-New Haven

Thu 2/18

4:34 pm-6:27 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sun 2/21

7:21 pm-10:39 pm

Nonstop2h 18m

$206

New HavenChicago

HVN Tweed-New Haven - ORD Chicago O'Hare Intl

HVNORD

Tweed-New Haven

Tue 12/29

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Thu 12/31

7:08 pm-10:31 pm

Nonstop2h 23m

$214

New HavenChicago

HVN Tweed-New Haven - ORD Chicago O'Hare Intl

HVNORD

Tweed-New Haven

Mon 12/7

6:44 pm-2:30 pm

2 stops20h 46m

Chicago O'Hare Intl

Thu 12/10

3:30 pm-7:04 pm

1 stop26h 34m

$298

New HavenChicago

HVN Tweed-New Haven - ORD Chicago O'Hare Intl

HVNORD

Tweed-New Haven

Fri 12/11

6:30 am-9:29 pm

1 stop15h 59m

Chicago O'Hare Intl

Sun 12/13

7:07 pm-10:30 pm

Nonstop2h 23m

$299

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Thu 1/7

6:00 am-11:32 am

1 stop6h 32m

Chicago O'Hare Intl

Sat 1/9

6:15 pm-9:37 pm

Nonstop2h 22m

$303

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Mon 12/14

6:00 am-11:33 am

1 stop6h 33m

Chicago O'Hare Intl

Wed 12/16

10:57 am-2:15 pm

Nonstop2h 18m

$303

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Mon 12/14

5:15 am-11:34 am

1 stop7h 19m

Chicago O'Hare Intl

Mon 12/14

8:30 pm-11:52 pm

Nonstop2h 22m

$307

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Tue 12/1

5:30 am-11:44 am

1 stop7h 14m

Chicago O'Hare Intl

Mon 12/7

8:10 am-11:23 am

Nonstop2h 13m

$307

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Fri 12/4

12:00 pm-11:33 pm

1 stop12h 33m

Chicago O'Hare Intl

Sat 12/5

2:59 pm-11:59 pm

1 stop8h 00m

$309

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Wed 12/2

12:00 pm-11:33 pm

1 stop12h 33m

Chicago O'Hare Intl

Sat 12/5

2:59 pm-11:59 pm

1 stop8h 00m

$309

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Connecticut averaging around $395.

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 Airport flights?

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

$62

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Connecticut in the past 72 hours is $62. The best round-trip flight deal from Connecticut to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $206.
The fastest flight from Connecticut to Chicago O'Hare Intl Airport takes 2h 30m
Direct flights go from Connecticut to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Connecticut to Chicago O'Hare Intl Airport

  • 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
JetBluePriceFrom $84Free CancellationRating
7.1
3,067 reviews
Search JetBlue flights
Avelo AirlinesPriceFrom $117Free CancellationRating
7.6
87 reviews
Search Avelo Airlines flights
American AirlinesPriceFrom $276Free CancellationRating
7.0
12,227 reviews
Search American Airlines flights
United AirlinesPriceFrom $289Free CancellationRating
7.3
10,471 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
Schaumburg
Merrillville
Rockford
South Haven
Oak Brook
Rosemont
Gurnee
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Skokie
Waukegan

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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