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.

$104 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

Fri, Sep 4 - Tue, Sep 8

4:25 pm - 9:35 pmLGA New York LaGuardia-MDW Chicago Midway

6h 10m1 stop Kansas City

4:40 pm - 11:15 pmMDW Chicago Midway-LGA New York LaGuardia

5h 35m1 stop Lambert-St Louis

$208Southwest

Mon, Oct 26 - Fri, Oct 30

7:45 pm - 11:55 pmLGA New York LaGuardia-MDW Chicago Midway

5h 10m1 stop Nashville Intl

2:25 pm - 9:25 pmMDW Chicago Midway-LGA New York LaGuardia

6h 00m1 stop Kansas City

$208Southwest

Thu, Sep 24 - 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

$208Frontier

Wed, Sep 30 - Thu, Oct 1

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

6h 36m1 stop Atlanta Hartsfield-Jackson

10:26 am - 8:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

9h 33m1 stop Atlanta Hartsfield-Jackson

$208Frontier

Sat, Sep 5 - Tue, Sep 8

6:11 am - 8:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

9:56 am - 3:30 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

4h 34m1 stop Washington, D.C. Reagan-National

$208American Airlines

Sat, Sep 5 - Tue, Sep 8

6:11 am - 8:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

9:56 am - 3:30 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

4h 34m1 stop Washington, D.C. Reagan-National

$208American Airlines

Sat, Sep 12 - Sat, Sep 19

12:59 pm - 7:01 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 02m1 stop Boston Logan Intl

6:30 am - 9:48 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 18mnonstop

$211JetBlue

Thu, Sep 10 - Mon, Sep 14

6:50 am - 1:45 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 55m1 stop Fort Lauderdale

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

2h 27mnonstop

$211JetBlue

Fri, Sep 18 - Tue, Sep 22

4:00 pm - 11:08 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

8h 08m1 stop Fort Lauderdale

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

8h 40m1 stop Atlanta Hartsfield-Jackson

$212Multiple Airlines

Sun, Sep 13 - Tue, Sep 15

6:00 am - 1:45 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

8h 45m1 stop Fort Lauderdale

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

8h 40m1 stop Atlanta Hartsfield-Jackson

$212Multiple Airlines

Recent last minute flight deals from Connecticut to Chicago

Sat, Aug 22 - Tue, Sep 1

5:55 am - 10:50 amEWR Newark-MDW Chicago Midway

5h 55m1 stop Atlanta Hartsfield-Jackson

11:50 am - 1:03 amMDW Chicago Midway-EWR Newark

12h 13m1 stop Atlanta Hartsfield-Jackson

$217Frontier

Tue, Aug 18 - Sat, Aug 22

10:29 pm - 7:53 amEWR Newark-ORD Chicago O'Hare Intl

10h 24m1 stop Atlanta Hartsfield-Jackson

1:59 pm - 1:03 amORD Chicago O'Hare Intl-EWR Newark

10h 04m1 stop Atlanta Hartsfield-Jackson

$220Frontier

Sat, Aug 22 - Tue, Sep 1

9:46 pm - 11:42 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 56mnonstop

11:10 am - 2:26 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$223American Airlines

Sat, Aug 22 - Tue, Sep 1

7:49 am - 11:38 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

4h 49m1 stop Washington, D.C. Reagan-National

11:10 am - 2:26 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$233American Airlines

Wed, Aug 19 - Wed, Sep 23

10:29 pm - 7:53 amEWR Newark-ORD Chicago O'Hare Intl

10h 24m1 stop Atlanta Hartsfield-Jackson

3:00 pm - 11:06 pmORD Chicago O'Hare Intl-EWR Newark

7h 06m1 stop Fort Lauderdale

$235Multiple Airlines

Fri, Aug 21 - Mon, Aug 31

6:00 am - 7:40 amEWR Newark-ORD Chicago O'Hare Intl

2h 40mnonstop

6:00 am - 9:07 amORD Chicago O'Hare Intl-EWR Newark

2h 07mnonstop

$255United Airlines

Sat, Aug 22 - Sat, Sep 19

9:45 pm - 11:22 pmEWR Newark-ORD Chicago O'Hare Intl

2h 37mnonstop

2:32 pm - 6:01 pmORD Chicago O'Hare Intl-EWR Newark

2h 29mnonstop

$267United Airlines

Wed, Aug 19 - Sun, Sep 6

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

2h 15mnonstop

5:25 am - 8:25 amMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$267Southwest

Thu, Aug 20 - Wed, Nov 25

1:35 pm - 8:15 pmEWR Newark-ORD Chicago O'Hare Intl

7h 40m1 stop Dallas/Fort Worth

3:20 pm - 11:55 pmORD Chicago O'Hare Intl-EWR Newark

7h 35m1 stop Fort Lauderdale

$276Multiple Airlines

Wed, Aug 19 - Sun, Sep 6

3:15 pm - 9:50 pmLGA New York LaGuardia-MDW Chicago Midway

7h 35m1 stop Lambert-St Louis

5:25 am - 8:25 amMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$277Southwest

Recent direct flight deals from Connecticut to Chicago

Fri, Oct 2 - Sun, Oct 4

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

$212JetBlue

Fri, Sep 18 - Sat, Sep 19

8:55 pm - 10:20 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

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

2h 10mnonstop

$213Southwest

Fri, Sep 18 - Mon, Sep 21

8:55 pm - 10:20 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

7:50 pm - 10:55 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$213Southwest

Fri, Sep 11 - Sun, Sep 13

7:35 pm - 9:37 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

6:00 am - 9:21 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$214JetBlue

Mon, Sep 7 - Thu, Sep 17

6:10 am - 7:50 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

1:00 pm - 4:19 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$217United Airlines

Sat, Aug 29 - Tue, Sep 1

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

2h 40mnonstop

6:00 pm - 9:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$218United Airlines

Sat, Aug 29 - Tue, Sep 1

9:46 pm - 11:42 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 56mnonstop

11:10 am - 2:26 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$218American Airlines

Thu, Aug 27 - Tue, Sep 1

8:29 pm - 10:30 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 01mnonstop

1:12 pm - 4:30 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 18mnonstop

$218American Airlines

Tue, Sep 1 - Wed, Sep 2

6:00 am - 7:29 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 29mnonstop

6:00 am - 9:09 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 09mnonstop

$237Delta

Tue, Sep 1 - Tue, Sep 1

6:00 am - 7:29 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 29mnonstop

8:12 pm - 11:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 32mnonstop

$237Delta

Useful Info

Low season	January
High season	July
Cheapest flight	$104

Best time to beat the crowds with an average 31% drop in price.

Most popular time to fly with an average 28% increase in price.

Flight from New York John F Kennedy Airport to Chicago O'Hare 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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Connecticut

First Class flights to Chicagofrom $620

Business Class flights to Chicagofrom $577

Premium Economy Class flights to Chicagofrom $615

Economy Class flights to Chicagofrom $117

$104 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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Connecticut

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight