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.

$109 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

Tue, Sep 22 - Tue, Sep 29

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

$222Frontier

Mon, Sep 28 - Tue, Sep 29

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

$222Frontier

Fri, Oct 16 - Mon, Oct 19

9:15 am - 2:32 pmEWR Newark-ORD Chicago O'Hare Intl

6h 17m1 stop Washington, D.C. Reagan-National

9:05 am - 5:17 pmORD Chicago O'Hare Intl-EWR Newark

7h 12m1 stop Boston Logan Intl

$229United Airlines

Sun, Oct 4 - Thu, Oct 8

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

2h 48mnonstop

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

2h 22mnonstop

$230JetBlue

Tue, Oct 6 - Sun, Oct 11

1:35 pm - 8:36 pmEWR Newark-ORD Chicago O'Hare Intl

8h 01m1 stop Fort Lauderdale

9:35 pm - 12:57 amORD Chicago O'Hare Intl-EWR Newark

2h 22mnonstop

$243United Airlines

Wed, Sep 30 - Sat, Oct 3

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 23 - Thu, Oct 1

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

Sat, Sep 19 - Sun, Sep 20

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

$248JetBlue

Sat, Oct 31 - Sat, Oct 31

7:00 am - 11:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

5h 00m1 stop Detroit Metropolitan Wayne County

1:45 pm - 5:06 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$251American Airlines

Sat, Oct 10 - Sat, Oct 10

7:00 am - 11:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

5h 00m1 stop Detroit Metropolitan Wayne County

12:52 pm - 4:17 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$251American Airlines

Recent last minute flight deals from Connecticut to Chicago

Wed, Sep 2 - Wed, Sep 16

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

10h 24m1 stop Atlanta Hartsfield-Jackson

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

8h 11m1 stop Orlando

$230Frontier

Wed, Sep 2 - Wed, Sep 16

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

10h 24m1 stop Atlanta Hartsfield-Jackson

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

8h 11m1 stop Orlando

$244Frontier

Sat, Sep 5 - Mon, Sep 21

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

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

2h 27mnonstop

$277JetBlue

Sat, Sep 5 - Sat, Sep 26

2:30 pm - 4:18 pmJFK 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 5 - Mon, Sep 21

1:00 pm - 8:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

8h 08m1 stop Atlanta Hartsfield-Jackson

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

2h 27mnonstop

$284Multiple Airlines

Sun, Sep 6 - Mon, Sep 21

11:25 am - 1:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:00 am - 9:15 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$286Delta

Sun, Sep 6 - Tue, Oct 6

11:25 am - 1:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:00 am - 9:12 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 12mnonstop

$286Delta

Sat, Sep 5 - Tue, Oct 6

6:58 am - 8:47 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

6:50 am - 10:05 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$286American Airlines

Sat, Sep 5 - Sat, Sep 26

3:59 pm - 5:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 58mnonstop

4:40 pm - 7:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$286American Airlines

Sun, Sep 6 - Tue, Oct 6

1:00 pm - 8:04 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

8h 04m1 stop Atlanta Hartsfield-Jackson

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

2h 28mnonstop

$293Multiple Airlines

Recent direct flight deals from Connecticut to Chicago

Sun, Oct 4 - Thu, Oct 8

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

2h 48mnonstop

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

2h 22mnonstop

$230JetBlue

Sat, Sep 19 - Sun, Sep 20

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

$248JetBlue

Sat, Feb 20 - Mon, Feb 22

7:00 am - 8:35 amPVD Providence-TFGreen-MDW Chicago Midway

2h 35mnonstop

5:45 pm - 8:55 pmMDW Chicago Midway-PVD Providence-TFGreen

2h 10mnonstop

$257Southwest

Tue, Nov 3 - Mon, Nov 9

6:10 pm - 7:45 pmPVD Providence-TFGreen-MDW Chicago Midway

2h 35mnonstop

5:20 pm - 8:30 pmMDW Chicago Midway-PVD Providence-TFGreen

2h 10mnonstop

$257Southwest

Thu, Oct 1 - Mon, Oct 5

11:31 am - 1:15 pmPVD Providence-TFGreen-ORD Chicago O'Hare Intl

2h 44mnonstop

7:03 am - 10:35 amORD Chicago O'Hare Intl-PVD Providence-TFGreen

2h 32mnonstop

$257United Airlines

Sat, Oct 17 - Tue, Oct 20

11:31 am - 1:14 pmPVD Providence-TFGreen-ORD Chicago O'Hare Intl

2h 43mnonstop

11:00 am - 2:40 pmORD Chicago O'Hare Intl-PVD Providence-TFGreen

2h 40mnonstop

$257United Airlines

Thu, Sep 17 - Mon, Sep 21

7:09 am - 9:05 amPVD Providence-TFGreen-ORD Chicago O'Hare Intl

2h 56mnonstop

7:48 pm - 11:21 pmORD Chicago O'Hare Intl-PVD Providence-TFGreen

2h 33mnonstop

$257American Airlines

Sat, Sep 26 - Sat, Oct 3

7:09 am - 9:05 amPVD Providence-TFGreen-ORD Chicago O'Hare Intl

2h 56mnonstop

7:48 pm - 11:21 pmORD Chicago O'Hare Intl-PVD Providence-TFGreen

2h 33mnonstop

$257American Airlines

Wed, Dec 9 - Wed, Dec 9

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

3h 00mnonstop

6:00 pm - 9:37 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 37mnonstop

$265Delta

Tue, Sep 22 - Fri, Sep 25

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

2h 29mnonstop

8:15 pm - 11:39 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$265Delta

Useful Info

Low season	January
High season	July
Cheapest flight	$109

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 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

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

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 $459

Premium Economy Class flights to Chicagofrom $615

Economy Class flights to Chicagofrom $117

$109 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