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.

$108 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

Sun, Sep 27 - Thu, Oct 1

4:30 pm - 9:47 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 17m1 stop Pittsburgh

7:46 am - 11:20 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 34mnonstop

$221American Airlines

Fri, Oct 23 - Mon, Oct 26

5:55 am - 7:02 pmEWR Newark-ORD Chicago O'Hare Intl

14h 07m1 stop Orlando

8:11 pm - 12:03 amORD Chicago O'Hare Intl-EWR Newark

26h 52m1 stop Orlando

$223Frontier

Mon, Nov 30 - Thu, Dec 3

8:30 pm - 10:37 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

9:00 am - 3:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

5h 59m1 stop Charlotte Douglas

$223American Airlines

Wed, Oct 7 - Fri, Oct 9

10:29 pm - 9:21 amEWR Newark-ORD Chicago O'Hare Intl

11h 52m1 stop Atlanta Hartsfield-Jackson

8:11 pm - 1:03 amORD Chicago O'Hare Intl-EWR Newark

27h 52m1 stop Orlando

$224Frontier

Fri, Sep 11 - Sun, Sep 13

8:05 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

6:00 am - 2:07 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 07m1 stop Fort Lauderdale

$228JetBlue

Tue, Sep 29 - Sat, Oct 3

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

2h 48mnonstop

3:00 pm - 11:51 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 51m1 stop Fort Lauderdale

$229JetBlue

Tue, Sep 15 - Wed, Sep 16

1:30 pm - 8:29 pmEWR Newark-ORD Chicago O'Hare Intl

7h 59m1 stop Dallas/Fort Worth

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

7h 06m1 stop Fort Lauderdale

$230Multiple Airlines

Fri, Oct 2 - Wed, Oct 7

3:38 pm - 11:08 pmEWR Newark-ORD Chicago O'Hare Intl

8h 30m1 stop Fort Lauderdale

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

8h 11m1 stop Orlando

$230Multiple Airlines

Tue, Sep 8 - Tue, Sep 8

8:05 am - 9:45 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

$237United Airlines

Tue, Nov 24 - Tue, Dec 1

10:16 am - 2:38 pmEWR Newark-ORD Chicago O'Hare Intl

5h 22m1 stop Washington, D.C. Dulles Intl

2:00 pm - 7:35 pmORD Chicago O'Hare Intl-EWR Newark

4h 35m1 stop Washington, D.C. Reagan-National

$239United Airlines

Recent last minute flight deals from Connecticut to Chicago

Sat, Aug 29 - Thu, Sep 24

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

$227Frontier

Sat, Aug 29 - Fri, Sep 25

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

$227Frontier

Thu, Aug 27 - Mon, Sep 28

7:00 am - 8:46 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 46mnonstop

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

2h 27mnonstop

$257JetBlue

Wed, Aug 26 - Wed, Sep 30

3:40 pm - 5:35 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

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

2h 21mnonstop

$264JetBlue

Wed, Aug 26 - Mon, Sep 28

2:59 pm - 4:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

4:01 pm - 7:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 28mnonstop

$266American Airlines

Wed, Aug 26 - Wed, Sep 30

5:25 pm - 7:29 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 04mnonstop

12:47 pm - 4:04 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$266American Airlines

Wed, Aug 26 - Mon, Sep 28

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

2h 15mnonstop

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

2h 05mnonstop

$266Southwest

Wed, Aug 26 - Wed, Sep 30

9:35 pm - 10:50 pmLGA New York LaGuardia-MDW Chicago Midway

2h 15mnonstop

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

2h 00mnonstop

$266Southwest

Sat, Aug 29 - Wed, Sep 23

2:30 pm - 4:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

7:00 am - 10:15 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$272Delta

Sat, Aug 29 - Mon, Sep 21

2:30 pm - 4:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

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

2h 15mnonstop

$272Delta

Recent direct flight deals from Connecticut to Chicago

Tue, Sep 8 - Tue, Sep 8

6:55 am - 8:42 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

6:23 pm - 9:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 36mnonstop

$230JetBlue

Tue, Sep 8 - Tue, Sep 8

8:05 am - 9:45 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

$237United Airlines

Tue, Sep 15 - Wed, Sep 16

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

2h 48mnonstop

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

2h 21mnonstop

$237JetBlue

Tue, Sep 8 - Thu, Sep 17

5:29 am - 7:15 amEWR Newark-ORD Chicago O'Hare Intl

2h 46mnonstop

6:39 am - 9:59 amORD Chicago O'Hare Intl-EWR Newark

2h 20mnonstop

$242American Airlines

Tue, Sep 8 - Thu, Sep 24

5:19 pm - 7:20 pmEWR Newark-ORD Chicago O'Hare Intl

3h 01mnonstop

8:38 pm - 11:59 pmORD Chicago O'Hare Intl-EWR Newark

2h 21mnonstop

$242American Airlines

Tue, Sep 8 - Sat, Sep 12

9:35 pm - 10:55 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

6:00 am - 9:00 amMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$242Southwest

Tue, Sep 8 - Sun, Sep 20

9:35 pm - 10:55 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

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

2h 00mnonstop

$242Southwest

Tue, Sep 8 - Mon, Sep 14

6:50 pm - 8:31 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 41mnonstop

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

2h 24mnonstop

$242Delta

Tue, Sep 8 - Sat, Sep 19

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

2h 45mnonstop

2:30 pm - 5:50 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$242Delta

Tue, Sep 8 - Mon, Sep 21

7:30 am - 9:13 amEWR Newark-ORD Chicago O'Hare Intl

2h 43mnonstop

5:00 am - 8:14 amORD Chicago O'Hare Intl-EWR Newark

2h 14mnonstop

$242United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$108

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

Most popular time to fly with an average 27% 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

Saint Joseph

Hammond

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

$108 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