Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Connecticut to Chicago from $59

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 9/13. 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

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
4:20 pm - 6:13 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
7:07 pm - 10:39 pm
ORD
-
HVN
2h 32mnonstop
$110Avelo Airlines
ven., mai 29 - lun., juin 1
Avelo Airlines Logo
3:50 pm - 5:43 pm
HVN
-
ORD
2h 53mnonstop
Avelo Airlines Logo
7:07 pm - 10:39 pm
ORD
-
HVN
2h 32mnonstop
$111Avelo Airlines
dim., juin 7 - lun., juin 8
Multiple Airlines Logo
10:00 pm - 7:55 am
LGA
-
ORD
10h 55m
1 stop
Multiple Airlines Logo
1:49 pm - 5:00 pm
ORD
-
LGA
2h 11mnonstop
$130Multiple Airlines
mar., mai 12 - jeu., mai 14
Spirit Airlines Logo
6:15 pm - 7:57 pm
LGA
-
ORD
2h 42mnonstop
Spirit Airlines Logo
1:49 pm - 5:00 pm
ORD
-
LGA
2h 11mnonstop
$131Spirit Airlines
mer., avr. 29 - lun., mai 4
Spirit Airlines Logo
10:08 am - 11:42 am
EWR
-
ORD
2h 34mnonstop
Spirit Airlines Logo
7:33 pm - 8:59 am
ORD
-
EWR
12h 26m
1 stop
$132Spirit Airlines
ven., mai 1 - lun., mai 4
Multiple Airlines Logo
10:00 pm - 7:55 am
LGA
-
ORD
10h 55m
1 stop
Multiple Airlines Logo
1:49 pm - 5:00 pm
ORD
-
LGA
2h 11mnonstop
$132Multiple Airlines
lun., mai 4 - jeu., mai 7
Frontier Logo
10:00 pm - 7:55 am
LGA
-
ORD
10h 55m
1 stop
Frontier Logo
6:55 am - 5:24 pm
ORD
-
LGA
9h 29m
1 stop
$140Frontier
mer., mai 6 - sam., mai 9
Frontier Logo
1:00 pm - 7:51 pm
JFK
-
ORD
7h 51m
1 stop
Frontier Logo
1:59 pm - 11:39 am
ORD
-
JFK
20h 40m
1 stop
$156Frontier
mer., mai 6 - mar., mai 12
JetBlue Logo
3:30 pm - 5:20 pm
JFK
-
ORD
2h 50mnonstop
JetBlue Logo
6:00 am - 9:17 am
ORD
-
JFK
2h 17mnonstop
$172JetBlue
mar., juil. 7 - lun., juil. 13
JetBlue Logo
3:30 pm - 5:22 pm
JFK
-
ORD
2h 52mnonstop
JetBlue Logo
9:39 am - 12:55 pm
ORD
-
JFK
2h 16mnonstop
$175JetBlue
mer., juil. 1 - mar., juil. 7

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
Apr 22
LGA6:15 pmNew York LaGuardia
2h 42m
ORD7:57 pmChicago O'Hare Intl
May 4
ORD1:49 pmChicago O'Hare Intl
2h 11m
LGA5:00 pmNew York LaGuardia
$131
Spirit Airlines
May 1
EWR10:08 amNewark
2h 34m
ORD11:42 amChicago O'Hare Intl
May 4
ORD7:33 pmChicago O'Hare Intl
12h 26m
1 stop
EWR8:59 amNewark
$132
Spirit Airlines
May 1
EWR10:08 amNewark
2h 34m
ORD11:42 amChicago O'Hare Intl
May 12
ORD5:05 amChicago O'Hare Intl
17h 47m
1 stop
EWR11:52 pmNewark
$133

Southwest flights from Connecticut to Chicago O'Hare Intl Airport

Our best Southwest deals on Connecticut to Chicago O'Hare Intl Airport flight tickets
Southwest
May 27
PVD7:15 amProvidence-TFGreen
9h 50m
1 stop
ORD4:05 pmChicago O'Hare Intl
Jun 1
ORD2:40 pmChicago O'Hare Intl
7h 45m
2 stops
PVD11:25 pmProvidence-TFGreen
$299
Southwest
May 1
PVD5:45 amProvidence-TFGreen
11h 20m
2 stops
ORD4:05 pmChicago O'Hare Intl
May 8
ORD2:40 pmChicago O'Hare Intl
7h 45m
2 stops
PVD11:25 pmProvidence-TFGreen
$496

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 avril 18, 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

Cheapest round-trip

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

ven. 5/29

4:20 pm-6:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

lun. 6/1

7:07 pm-10:39 pm

Nonstop2h 32m

$110

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

dim. 6/7

3:50 pm-5:43 pm

Nonstop2h 53m

Chicago O'Hare Intl

lun. 6/8

7:07 pm-10:39 pm

Nonstop2h 32m

$111

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mar. 5/12

10:00 pm-7:55 am

1 stop10h 55m

Chicago O'Hare Intl

jeu. 5/14

1:49 pm-5:00 pm

Nonstop2h 11m

$130
Quickest round-trip

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mer. 4/29

6:15 pm-7:57 pm

Nonstop2h 42m

Chicago O'Hare Intl

lun. 5/4

1:49 pm-5:00 pm

Nonstop2h 11m

$131

NewarkChicago

EWR - ORD

EWRORD

Newark

ven. 5/1

10:08 am-11:42 am

Nonstop2h 34m

Chicago O'Hare Intl

lun. 5/4

7:33 pm-8:59 am

1 stop12h 26m

$132

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

lun. 5/4

10:00 pm-7:55 am

1 stop10h 55m

Chicago O'Hare Intl

jeu. 5/7

1:49 pm-5:00 pm

Nonstop2h 11m

$132

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mer. 5/6

10:00 pm-7:55 am

1 stop10h 55m

Chicago O'Hare Intl

sam. 5/9

6:55 am-5:24 pm

1 stop9h 29m

$140

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mer. 5/6

1:00 pm-7:51 pm

1 stop7h 51m

Chicago O'Hare Intl

mar. 5/12

1:59 pm-11:39 am

1 stop20h 40m

$156

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mar. 7/7

3:30 pm-5:20 pm

Nonstop2h 50m

Chicago O'Hare Intl

lun. 7/13

6:00 am-9:17 am

Nonstop2h 17m

$172

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mer. 7/1

3:30 pm-5:22 pm

Nonstop2h 52m

Chicago O'Hare Intl

mar. 7/7

9:39 am-12:55 pm

Nonstop2h 16m

$175

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $305.

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

$132

Fastest flight time

2h 26m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Connecticut in the past 72 hours is $132. The best round-trip flight deal from Connecticut to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $130.
The fastest flight from Connecticut to Chicago O'Hare Intl Airport takes 2h 26m
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
Avelo AirlinesPriceFrom $77Free CancellationRating
7.6
88 reviews
Search Avelo Airlines flights
American AirlinesPriceFrom $159Free CancellationRating
7.1
11,618 reviews
Search American Airlines flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,603 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
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Elgin
Tinley Park
Evanston

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.

An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
lun. 5/18
lun. 5/25
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago