How does KAYAK find such low prices on flights from Connecticut to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Connecticut to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Connecticut to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Connecticut is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Connecticut to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Connecticut with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Connecticut to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$111 CHEAP FLIGHTS from Connecticut to Chicago

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Cheap Flights from Connecticut to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Connecticut to Chicago

Wed, Sep 23 - Tue, Sep 29

6:15 am - 11:51 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 36m1 stop Atlanta Hartsfield-Jackson

6:00 am - 7:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

12h 44m1 stop Dallas/Fort Worth

$222Frontier

Wed, Sep 23 - Wed, Sep 30

6:15 am - 6:23 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

13h 08m1 stop Atlanta Hartsfield-Jackson

6:20 am - 4:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

8h 40m1 stop Atlanta Hartsfield-Jackson

$222Frontier

Sat, Oct 17 - Tue, Oct 20

1:00 pm - 7:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 14m1 stop Boston Logan Intl

9:38 am - 5:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

6h 51m1 stop Boston Logan Intl

$235JetBlue

Thu, Oct 22 - Thu, Oct 22

6:00 am - 7:42 amEWR Newark-ORD Chicago O'Hare Intl

2h 42mnonstop

11:15 am - 4:30 pmORD Chicago O'Hare Intl-EWR Newark

4h 15m1 stop Washington, D.C. Reagan-National

$238United Airlines

Fri, Nov 13 - Sat, Nov 14

11:20 am - 1:11 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

3:00 pm - 6:19 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$243United Airlines

Tue, Sep 22 - Wed, Sep 30

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

10:59 am - 2:20 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$244Multiple Airlines

Wed, Sep 30 - Mon, Oct 5

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$244Multiple Airlines

Sat, Oct 17 - Tue, Oct 20

1:00 pm - 7:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 14m1 stop Boston Logan Intl

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$251JetBlue

Sat, Nov 14 - Sat, Nov 14

7:12 am - 8:59 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 47mnonstop

10:30 am - 3:55 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

4h 25m1 stop Detroit Metropolitan Wayne County

$256American Airlines

Tue, Sep 29 - Wed, Sep 30

9:17 am - 11:05 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

11:29 am - 2:43 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 14mnonstop

$267American Airlines

Recent last minute flight deals from Connecticut to Chicago

Sat, Sep 12 - Fri, Sep 25

10:29 pm - 9:20 amEWR Newark-ORD Chicago O'Hare Intl

11h 51m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 1:01 amORD Chicago O'Hare Intl-EWR Newark

8h 11m1 stop Orlando

$240Frontier

Thu, Sep 10 - Tue, Sep 15

10:29 pm - 9:20 amEWR Newark-ORD Chicago O'Hare Intl

11h 51m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 1:01 amORD Chicago O'Hare Intl-EWR Newark

8h 11m1 stop Orlando

$246Frontier

Thu, Sep 10 - Mon, Sep 14

7:20 am - 9:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

3:00 pm - 6:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$277United Airlines

Sat, Sep 12 - Sun, Sep 13

8:27 pm - 10:11 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

4:00 pm - 7:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$277United Airlines

Thu, Sep 10 - Mon, Sep 28

8:10 am - 9:58 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$277JetBlue

Sat, Sep 12 - Sun, Sep 27

10:04 pm - 11:50 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 46mnonstop

6:00 am - 9:14 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 14mnonstop

$286American Airlines

Sat, Sep 12 - Sat, Sep 19

8:10 am - 9:58 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$292JetBlue

Thu, Sep 10 - Mon, Sep 28

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$293Multiple Airlines

Thu, Sep 10 - Sat, Oct 24

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$293Multiple Airlines

Sat, Sep 12 - Sun, Sep 27

7:30 am - 11:41 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

5h 11m1 stop Washington, D.C. Reagan-National

6:59 am - 10:10 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 11mnonstop

$296American Airlines

Recent direct flight deals from Connecticut to Chicago

Fri, Nov 13 - Sat, Nov 14

11:20 am - 1:11 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

3:00 pm - 6:19 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$243United Airlines

Thu, Oct 29 - Thu, Nov 5

2:30 pm - 4:21 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

7:00 am - 10:09 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 09mnonstop

$243United Airlines

Fri, Oct 16 - Mon, Oct 19

8:15 pm - 10:10 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$258JetBlue

Sat, Oct 17 - Sun, Oct 18

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$258JetBlue

Tue, Oct 6 - Wed, Oct 7

6:59 pm - 8:43 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

8:20 pm - 11:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$267Delta

Tue, Oct 20 - Tue, Nov 3

6:00 am - 7:36 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 36mnonstop

7:00 am - 10:17 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$267Delta

Tue, Sep 29 - Wed, Sep 30

9:17 am - 11:05 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

11:29 am - 2:43 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 14mnonstop

$267American Airlines

Sat, Sep 26 - Sun, Sep 27

7:59 am - 9:52 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 53mnonstop

6:00 am - 9:14 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 14mnonstop

$267American Airlines

Sat, Oct 3 - Mon, Oct 5

9:25 am - 10:55 amLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

5:10 am - 8:15 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$267Southwest

Fri, Oct 16 - Mon, Oct 19

9:00 pm - 10:25 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

7:35 pm - 10:45 pmMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$267Southwest

Useful Info

Low season	January
High season	July
Cheapest flight	$111

Best time to beat the crowds with an average 32% drop in price.

Most popular time to fly with an average 26% increase in price.

Flight from Newark Liberty Airport to Chicago Midway Airport

How does KAYAK find such low prices on flights from Connecticut to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Connecticut to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Connecticut to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Connecticut is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Connecticut to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Connecticut with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Connecticut to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

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$111 Find Cheap Flights from Connecticut to Chicago - Compare and Save

Cheap Flights from Connecticut to Chicago

Recent round-trip flight deals from Connecticut to Chicago

Recent one-way flight deals from Connecticut to Chicago

Recent last minute flight deals from Connecticut to Chicago

Recent direct flight deals from Connecticut to Chicago

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Connecticut to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Connecticut

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Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight