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.

$93 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 30 - Wed, Oct 7

6:15 am - 5:51 pmLGA New York LaGuardia-MDW Chicago Midway

12h 36m1 stop Atlanta Hartsfield-Jackson

6:25 am - 4:00 pmMDW Chicago Midway-LGA New York LaGuardia

8h 35m1 stop Atlanta Hartsfield-Jackson

$228Frontier

Wed, Oct 21 - Thu, Oct 22

6:30 am - 10:07 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

4h 37m1 stop Washington, D.C. Reagan-National

4:26 pm - 8:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 34mnonstop

$232American Airlines

Fri, Oct 23 - Mon, Nov 2

4:20 pm - 10:00 pmLGA New York LaGuardia-MDW Chicago Midway

6h 40m1 stop Kansas City

9:35 am - 12:40 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$233Southwest

Fri, Oct 23 - Mon, Oct 26

4:20 pm - 8:55 pmLGA New York LaGuardia-MDW Chicago Midway

5h 35m1 stop Kansas City

5:10 pm - 8:15 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$233Southwest

Thu, Oct 1 - Sat, Oct 3

6:15 am - 5:46 pmLGA New York LaGuardia-MDW Chicago Midway

12h 31m1 stop Atlanta Hartsfield-Jackson

6:25 am - 4:00 pmMDW Chicago Midway-LGA New York LaGuardia

8h 35m1 stop Atlanta Hartsfield-Jackson

$234Frontier

Wed, Oct 14 - Fri, Oct 16

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

$235JetBlue

Mon, Oct 5 - Tue, Oct 6

1:00 pm - 7:03 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 03m1 stop Boston Logan Intl

7:05 am - 10:33 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 28mnonstop

$235JetBlue

Tue, Dec 22 - Wed, Jan 6

10:15 am - 12:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

10:40 am - 2:04 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 24mnonstop

$235Delta

Tue, Dec 22 - Tue, Jan 5

10:15 am - 12:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

1:30 pm - 4:55 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$235Delta

Sun, Nov 8 - Tue, Nov 10

8:24 pm - 10:30 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

10:31 am - 1:58 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$235American Airlines

Recent last minute flight deals from Connecticut to Chicago

Wed, Sep 16 - Fri, Sep 18

11:35 am - 6:23 pmEWR Newark-ORD Chicago O'Hare Intl

7h 48m1 stop Atlanta Hartsfield-Jackson

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

8h 11m1 stop Orlando

$245Frontier

Mon, Sep 21 - Sat, Sep 26

1:30 pm - 12:45 amEWR Newark-ORD Chicago O'Hare Intl

12h 15m1 stop Dallas/Fort Worth

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

8h 11m1 stop Orlando

$246Frontier

Thu, Sep 17 - Tue, Oct 6

6:59 am - 8:51 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 52mnonstop

6:29 pm - 9:57 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 28mnonstop

$254American Airlines

Thu, Sep 17 - Tue, Oct 6

6:55 am - 8:48 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

10:34 am - 1:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$254American Airlines

Thu, Sep 17 - Tue, Oct 6

7:15 am - 12:59 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 44m1 stop Detroit Metropolitan Wayne County

6:00 pm - 9:40 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 40mnonstop

$264Delta

Wed, Sep 16 - Fri, Oct 16

9:10 am - 10:54 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

7:45 pm - 11:10 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$280United Airlines

Sat, Sep 19 - Sat, Nov 21

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

2h 40mnonstop

6:26 pm - 9:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 33mnonstop

$286United Airlines

Sat, Sep 19 - Wed, Sep 23

5:30 pm - 7:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

2:29 pm - 5:50 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$293Delta

Sat, Sep 19 - Sat, Sep 26

5:50 pm - 7:20 pmLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

3:10 pm - 6:15 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$301Southwest

Thu, Sep 17 - Sat, Sep 19

6:00 am - 7:15 amLGA New York LaGuardia-MDW Chicago Midway

2h 15mnonstop

12:10 pm - 3:20 pmMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$305Southwest

Recent direct flight deals from Connecticut to Chicago

Sun, Nov 8 - Tue, Nov 10

8:24 pm - 10:30 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

10:31 am - 1:58 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$235American Airlines

Wed, Nov 18 - Sun, Nov 22

7:29 am - 9:30 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

10:37 am - 2:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 23mnonstop

$235American Airlines

Wed, Oct 14 - Fri, Oct 16

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

$235JetBlue

Tue, Dec 22 - Wed, Jan 6

10:15 am - 12:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

10:40 am - 2:04 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 24mnonstop

$235Delta

Tue, Dec 22 - Tue, Jan 5

10:15 am - 12:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

1:30 pm - 4:55 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$235Delta

Wed, Oct 7 - Sun, Oct 11

9:10 am - 10:54 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

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

2h 17mnonstop

$235United Airlines

Fri, Feb 12 - Fri, Feb 12

8:15 am - 10:04 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

6:30 pm - 9:45 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$235United Airlines

Sun, Nov 8 - Tue, Nov 10

6:45 am - 8:10 amLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

4:55 pm - 8:00 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$235Southwest

Wed, Oct 7 - Sun, Oct 11

9:05 pm - 10:30 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

5:05 am - 8:10 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$235Southwest

Sat, Oct 3 - Wed, Oct 7

8:15 pm - 10:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

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

2h 21mnonstop

$236JetBlue

Useful Info

Low season	January
High season	July
Cheapest flight	$93

Best time to beat the crowds with an average 33% drop in price.

Most popular time to fly with an average 25% increase in price.

Flight from New York LaGuardia 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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$93 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

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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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Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight