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Cheap flights from Connecticut to Chicago from $52

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 7/31. 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
8:42 am - 10:20 am
LGA
-
ORD
2h 38mnonstop
Spirit Airlines Logo
7:31 pm - 10:36 pm
ORD
-
LGA
2h 05mnonstop
$84Spirit Airlines
Mon, Mar 23 - Mon, Mar 30
Frontier Logo
4:29 pm - 6:29 pm
JFK
-
ORD
3h 00mnonstop
Frontier Logo
8:06 am - 11:30 am
ORD
-
JFK
2h 24mnonstop
$85Frontier
Mon, Mar 16 - Tue, Mar 31
Multiple Airlines Logo
10:54 pm - 12:22 am
EWR
-
ORD
2h 28mnonstop
Multiple Airlines Logo
11:07 am - 9:29 pm
ORD
-
EWR
9h 22m
1 stop
$96Multiple Airlines
Tue, Apr 7 - Tue, Apr 14
Avelo Airlines Logo
4:40 pm - 6:33 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
7:18 pm - 10:49 pm
ORD
-
HVN
2h 31mnonstop
$103Avelo Airlines
Fri, Aug 28 - Mon, Aug 31
Avelo Airlines Logo
4:10 pm - 6:03 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
6:48 pm - 10:19 pm
ORD
-
HVN
2h 31mnonstop
$111Avelo Airlines
Fri, Jul 10 - Mon, Jul 13
Multiple Airlines Logo
8:36 pm - 9:05 am
HVN
-
ORD
13h 29m
1 stop
Multiple Airlines Logo
4:38 pm - 12:26 pm
ORD
-
HVN
18h 48m
2 stops
$195Multiple Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
6:53 am - 8:45 am
BDL
-
ORD
2h 52mnonstop
American Airlines Logo
3:20 pm - 6:39 pm
ORD
-
BDL
2h 19mnonstop
$295American Airlines
Thu, Apr 2 - Tue, Apr 7
United Airlines Logo
6:00 am - 9:38 am
BDL
-
ORD
4h 38m
1 stop
United Airlines Logo
11:00 am - 2:15 pm
ORD
-
BDL
2h 15mnonstop
$298United Airlines
Sat, Apr 4 - Thu, Apr 9
United Airlines Logo
10:33 am - 4:30 pm
BDL
-
ORD
6h 57m
1 stop
United Airlines Logo
11:02 am - 2:18 pm
ORD
-
BDL
2h 16mnonstop
$303United Airlines
Wed, May 13 - Sat, May 16
American Airlines Logo
11:59 am - 1:58 pm
PVD
-
ORD
2h 59mnonstop
American Airlines Logo
1:48 pm - 5:12 pm
ORD
-
PVD
2h 24mnonstop
$311American Airlines
Mon, Apr 6 - Wed, Apr 8

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

Our best Spirit Airlines deals on Connecticut to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Mar 23
LGA8:42 amNew York LaGuardia
2h 38m
ORD10:20 amChicago O'Hare Intl
Mar 30
ORD7:31 pmChicago O'Hare Intl
2h 05m
LGA10:36 pmNew York LaGuardia
$84
Spirit Airlines
Apr 13
LGA6:30 amNew York LaGuardia
2h 31m
ORD8:01 amChicago O'Hare Intl
Apr 20
ORD2:09 pmChicago O'Hare Intl
2h 11m
LGA5:20 pmNew York LaGuardia
$85
Spirit Airlines
Apr 28
LGA6:15 pmNew York LaGuardia
2h 42m
ORD7:57 pmChicago O'Hare Intl
May 4
ORD2:09 pmChicago O'Hare Intl
2h 11m
LGA5:20 pmNew York LaGuardia
$86

Frontier flights from Connecticut to Chicago O'Hare Intl Airport

Our best Frontier deals on Connecticut to Chicago O'Hare Intl Airport flight tickets
Frontier
Mar 16
JFK4:29 pmNew York John F Kennedy Intl
3h 00m
ORD6:29 pmChicago O'Hare Intl
Mar 31
ORD8:06 amChicago O'Hare Intl
2h 24m
JFK11:30 amNew York John F Kennedy Intl
$85
Frontier
Mar 19
JFK4:29 pmNew York John F Kennedy Intl
3h 00m
ORD6:29 pmChicago O'Hare Intl
Mar 23
ORD12:05 pmChicago O'Hare Intl
2h 24m
JFK3:29 pmNew York John F Kennedy Intl
$86
Frontier
Mar 25
JFK4:29 pmNew York John F Kennedy Intl
3h 00m
ORD6:29 pmChicago O'Hare Intl
Mar 31
ORD8:06 amChicago O'Hare Intl
2h 24m
JFK11:30 amNew York John F Kennedy Intl
$87

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 March 3, 2026.
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

Mon 3/23

8:42 am-10:20 am

Nonstop2h 38m

Chicago O'Hare Intl

Mon 3/30

7:31 pm-10:36 pm

Nonstop2h 05m

$84

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 3/16

4:29 pm-6:29 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 3/31

8:06 am-11:30 am

Nonstop2h 24m

$85

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 4/7

10:54 pm-12:22 am

Nonstop2h 28m

Chicago O'Hare Intl

Tue 4/14

11:07 am-9:29 pm

1 stop9h 22m

$96

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 8/28

4:40 pm-6:33 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 8/31

7:18 pm-10:49 pm

Nonstop2h 31m

$103

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 7/10

4:10 pm-6:03 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 7/13

6:48 pm-10:19 pm

Nonstop2h 31m

$111

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Thu 5/14

8:36 pm-9:05 am

1 stop13h 29m

Chicago O'Hare Intl

Mon 5/18

4:38 pm-12:26 pm

2 stops18h 48m

$195

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 4/2

6:53 am-8:45 am

Nonstop2h 52m

Chicago O'Hare Intl

Tue 4/7

3:20 pm-6:39 pm

Nonstop2h 19m

$295

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 4/4

6:00 am-9:38 am

1 stop4h 38m

Chicago O'Hare Intl

Thu 4/9

11:00 am-2:15 pm

Nonstop2h 15m

$298

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 5/13

10:33 am-4:30 pm

1 stop6h 57m

Chicago O'Hare Intl

Sat 5/16

11:02 am-2:18 pm

Nonstop2h 16m

$303

ProvidenceChicago

PVD - ORD

PVDORD

Providence-TFGreen

Mon 4/6

11:59 am-1:58 pm

Nonstop2h 59m

Chicago O'Hare Intl

Wed 4/8

1:48 pm-5:12 pm

Nonstop2h 24m

$311

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 September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Connecticut averaging around $306.

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

$204

Fastest flight time

2h 28m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Connecticut in the past 72 hours is $204. The best round-trip flight deal from Connecticut to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $111.
The fastest flight from Connecticut to Chicago O'Hare Intl Airport takes 2h 28m
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
Avelo AirlinesPriceFrom $76Free CancellationRating
7.6
88 reviews
Search Avelo Airlines flights
American AirlinesPriceFrom $171Free CancellationRating
7.1
11,377 reviews
Search American Airlines flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,382 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
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

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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