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Cheap flights from Connecticut to Chicago from $97

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
2:40 pm - 4:33 pmHVN  Tweed-New Haven-ORD Chicago O'Hare Intl
2h 53mnonstop
Avelo Airlines Logo
7:17 pm - 10:39 pmORD  Chicago O'Hare Intl-HVN Tweed-New Haven
2h 22mnonstop
$193Avelo Airlines
Wed, Oct 28 - Fri, Oct 30
Avelo Airlines Logo
4:45 pm - 6:28 pmHVN  Tweed-New Haven-ORD Chicago O'Hare Intl
2h 43mnonstop
Avelo Airlines Logo
7:17 pm - 10:39 pmORD  Chicago O'Hare Intl-HVN Tweed-New Haven
2h 22mnonstop
$219Avelo Airlines
Mon, Oct 26 - Fri, Oct 30
Multiple Airlines Logo
2:40 pm - 4:33 pmHVN  Tweed-New Haven-ORD Chicago O'Hare Intl
2h 53mnonstop
Multiple Airlines Logo
7:44 pm - 10:19 pmORD  Chicago O'Hare Intl-HVN Tweed-New Haven
25h 35m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
$277Multiple Airlines
Wed, Oct 21 - Wed, Oct 21
Multiple Airlines Logo
2:40 pm - 4:33 pmHVN  Tweed-New Haven-ORD Chicago O'Hare Intl
2h 53mnonstop
Multiple Airlines Logo
7:44 pm - 10:19 pmORD  Chicago O'Hare Intl-HVN Tweed-New Haven
25h 35m3 stops Atlanta Hartsfield-Jackson Orlando Baltimore/Washington
$279Multiple Airlines
Wed, Oct 21 - Wed, Oct 21
JetBlue Logo
6:25 am - 11:24 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
5h 59m1 stop New York John F Kennedy Intl
JetBlue Logo
2:55 pm - 11:58 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
8h 03m1 stop Fort Lauderdale
$289JetBlue
Wed, Oct 21 - Sat, Oct 24
JetBlue Logo
6:25 am - 11:24 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
5h 59m1 stop New York John F Kennedy Intl
JetBlue Logo
2:55 pm - 11:58 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
8h 03m1 stop Fort Lauderdale
$289JetBlue
Thu, Oct 22 - Sat, Oct 24
American Airlines Logo
12:22 pm - 2:10 pmBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
2h 48mnonstop
American Airlines Logo
8:30 pm - 11:48 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 18mnonstop
$297American Airlines
Mon, Nov 2 - Mon, Nov 2
American Airlines Logo
7:15 am - 9:05 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
2h 50mnonstop
American Airlines Logo
7:59 pm - 11:24 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 25mnonstop
$297American Airlines
Thu, Oct 29 - Sat, Oct 31
United Airlines Logo
5:03 pm - 6:48 pmBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
2h 45mnonstop
United Airlines Logo
2:30 pm - 5:53 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 23mnonstop
$297United Airlines
Wed, Oct 21 - Sat, Oct 24
United Airlines Logo
5:03 pm - 6:48 pmBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
2h 45mnonstop
United Airlines Logo
2:30 pm - 5:53 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 23mnonstop
$297United Airlines
Wed, Oct 21 - Sat, Oct 24

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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
Oct 26
HVN4:45 pmTweed-New Haven
2h 43m
ORD6:28 pmChicago O'Hare Intl
Oct 30
ORD7:17 pmChicago O'Hare Intl
2h 22m
HVN10:39 pmTweed-New Haven
$219
Avelo Airlines
Oct 28
HVN2:40 pmTweed-New Haven
2h 53m
ORD4:33 pmChicago O'Hare Intl
Oct 30
ORD7:17 pmChicago O'Hare Intl
2h 22m
HVN10:39 pmTweed-New Haven
$233
Avelo Airlines
Sep 30
HVN3:25 pmTweed-New Haven
2h 53m
ORD5:18 pmChicago O'Hare Intl
Oct 2
ORD7:17 pmChicago O'Hare Intl
2h 22m
HVN10:39 pmTweed-New Haven
$253

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
Oct 22
BDL6:25 amHartford Bradley Intl
5h 59m
1 stop
ORD11:24 amChicago O'Hare Intl
Oct 26
ORD2:42 pmChicago O'Hare Intl
8h 17m
1 stop
BDL11:59 pmHartford Bradley Intl
$289
JetBlue
Oct 22
BDL6:25 amHartford Bradley Intl
5h 59m
1 stop
ORD11:24 amChicago O'Hare Intl
Oct 26
ORD2:42 pmChicago O'Hare Intl
8h 17m
1 stop
BDL11:59 pmHartford Bradley Intl
$291
JetBlue
Oct 21
BDL6:25 amHartford Bradley Intl
5h 59m
1 stop
ORD11:24 amChicago O'Hare Intl
Oct 24
ORD2:55 pmChicago O'Hare Intl
8h 03m
1 stop
BDL11:58 pmHartford Bradley Intl
$292

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

New HavenChicago

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

HVNORD

Tweed-New Haven

Wed 10/28

2:40 pm-4:33 pm

Nonstop2h 53m

Chicago O'Hare Intl

Fri 10/30

7:17 pm-10:39 pm

Nonstop2h 22m

$193
Quickest round-trip

New HavenChicago

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

HVNORD

Tweed-New Haven

Mon 10/26

4:45 pm-6:28 pm

Nonstop2h 43m

Chicago O'Hare Intl

Fri 10/30

7:17 pm-10:39 pm

Nonstop2h 22m

$219

New HavenChicago

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

HVNORD

Tweed-New Haven

Wed 10/21

2:40 pm-4:33 pm

Nonstop2h 53m

Chicago O'Hare Intl

Wed 10/21

7:44 pm-10:19 pm

2 stops25h 35m

$277

New HavenChicago

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

HVNORD

Tweed-New Haven

Wed 10/21

2:40 pm-4:33 pm

Nonstop2h 53m

Chicago O'Hare Intl

Wed 10/21

7:44 pm-10:19 pm

3 stops25h 35m

$279

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Wed 10/21

6:25 am-11:24 am

1 stop5h 59m

Chicago O'Hare Intl

Sat 10/24

2:55 pm-11:58 pm

1 stop8h 03m

$289

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Thu 10/22

6:25 am-11:24 am

1 stop5h 59m

Chicago O'Hare Intl

Sat 10/24

2:55 pm-11:58 pm

1 stop8h 03m

$289

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Mon 11/2

12:22 pm-2:10 pm

Nonstop2h 48m

Chicago O'Hare Intl

Mon 11/2

8:30 pm-11:48 pm

Nonstop2h 18m

$297

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Thu 10/29

7:15 am-9:05 am

Nonstop2h 50m

Chicago O'Hare Intl

Sat 10/31

7:59 pm-11:24 pm

Nonstop2h 25m

$297

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Wed 10/21

5:03 pm-6:48 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sat 10/24

2:30 pm-5:53 pm

Nonstop2h 23m

$297

HartfordChicago

BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl

BDLORD

Hartford Bradley Intl

Wed 10/21

5:03 pm-6:48 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sat 10/24

2:30 pm-5:53 pm

Nonstop2h 23m

$297

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 December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Connecticut averaging around $384.

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

$97

Fastest flight time

2h 31m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Connecticut in the past 72 hours is $97. The best round-trip flight deal from Connecticut to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $193.
The fastest flight from Connecticut to Chicago O'Hare Intl Airport takes 2h 31m
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
3,038 reviews
Search JetBlue flights
Avelo AirlinesPriceFrom $117Free CancellationRating
7.5
85 reviews
Search Avelo Airlines flights
DeltaPriceFrom $176Free CancellationRating
7.8
8,594 reviews
Search Delta flights
American AirlinesPriceFrom $249Free CancellationRating
7.0
12,077 reviews
Search American Airlines flights
United AirlinesPriceFrom $276Free CancellationRating
7.4
10,229 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
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Evanston
Skokie

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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