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.

$107 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

Mon, Nov 2 - Mon, Nov 9

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

7:17 pm - 10:39 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

$224Avelo Airlines

Mon, Nov 2 - Mon, Nov 9

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

7:17 pm - 10:39 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

$227Avelo Airlines

Thu, Nov 19 - Sat, Nov 21

12:10 pm - 2:05 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

8:10 am - 11:20 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 10mnonstop

$299American Airlines

Wed, Oct 28 - Wed, Oct 28

1:25 pm - 2:45 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

4:45 pm - 10:20 pmMDW Chicago Midway-BDL Hartford Bradley Intl

4h 35m1 stop Baltimore/Washington

$300Southwest

Sat, Dec 12 - Mon, Dec 14

8:40 am - 5:15 pmBDL Hartford Bradley Intl-MDW Chicago Midway

9h 35m2 stops Baltimore/Washington Tampa

1:20 pm - 10:05 pmMDW Chicago Midway-BDL Hartford Bradley Intl

7h 45m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington

$302Southwest

Fri, Dec 11 - Tue, Dec 15

6:00 am - 11:33 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

6h 33m1 stop Washington, D.C. Dulles Intl

2:15 pm - 5:33 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

$302United Airlines

Sat, Nov 21 - Tue, Dec 1

7:03 am - 9:05 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

4:56 pm - 11:36 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

5h 40m1 stop Washington, D.C. Reagan-National

$303American Airlines

Mon, Nov 23 - Fri, Nov 27

10:37 am - 5:00 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

7h 23m1 stop Washington, D.C. Dulles Intl

6:25 pm - 9:47 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 22mnonstop

$303United Airlines

Wed, Oct 28 - Tue, Nov 3

2:40 pm - 4:33 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

7:35 pm - 12:53 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

16h 18m1 stop Atlanta Hartsfield-Jackson

$306Multiple Airlines

Wed, Oct 28 - Thu, Oct 29

7:00 am - 12:51 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

6h 51m1 stop Atlanta Hartsfield-Jackson

7:39 pm - 10:59 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 20mnonstop

$307Multiple Airlines

Recent last minute flight deals from Connecticut to Chicago

Mon, Oct 12 - Mon, Nov 9

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

7:17 pm - 10:39 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

$277Avelo Airlines

Sat, Oct 10 - Sat, Oct 17

6:25 am - 11:24 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

5h 59m1 stop New York John F Kennedy Intl

2:55 pm - 11:58 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

8h 03m1 stop Fort Lauderdale

$375JetBlue

Mon, Oct 12 - Sat, Oct 17

6:25 am - 11:24 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

5h 59m1 stop New York John F Kennedy Intl

2:55 pm - 11:58 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

8h 03m1 stop Fort Lauderdale

$375JetBlue

Mon, Oct 12 - Thu, Oct 15

3:16 pm - 7:51 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

17h 35m1 stop Orlando

6:58 pm - 2:21 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

18h 23m1 stop Orlando

$404Frontier

Mon, Oct 12 - Mon, Nov 9

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

6:00 am - 10:59 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

15h 59m3 stops Baltimore/Washington Atlanta Hartsfield-Jackson Jacksonville

$404Multiple Airlines

Thu, Oct 8 - Fri, Oct 9

5:15 pm - 6:54 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 39mnonstop

7:17 pm - 10:39 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

$451Avelo Airlines

Sat, Oct 10 - Sun, Oct 11

7:40 pm - 7:25 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

12h 45m2 stops Washington, D.C. Dulles Intl Syracuse Hancock Intl

11:06 am - 2:29 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 23mnonstop

$524United Airlines

Sat, Oct 10 - Sun, Oct 11

7:40 pm - 7:25 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

12h 45m2 stops Washington, D.C. Dulles Intl Syracuse Hancock Intl

11:06 am - 2:29 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 23mnonstop

$524United Airlines

Sat, Oct 10 - Tue, Oct 13

5:38 pm - 7:59 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

3h 21mnonstop

8:21 am - 11:42 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 21mnonstop

$527American Airlines

Sat, Oct 10 - Tue, Oct 13

7:15 am - 9:05 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 50mnonstop

7:59 pm - 11:24 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 25mnonstop

$527American Airlines

Recent direct flight deals from Connecticut to Chicago

Mon, Nov 2 - Mon, Nov 9

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

7:17 pm - 10:39 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

$224Avelo Airlines

Mon, Nov 2 - Mon, Nov 9

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

7:17 pm - 10:39 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

$227Avelo Airlines

Fri, Nov 6 - Fri, Nov 13

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

7:17 pm - 10:39 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

$234Avelo Airlines

Thu, Nov 19 - Sat, Nov 21

12:10 pm - 2:05 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

8:10 am - 11:20 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 10mnonstop

$299American Airlines

Mon, Nov 2 - Mon, Nov 9

6:40 pm - 8:05 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 25mnonstop

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

$305Southwest

Mon, Nov 2 - Mon, Nov 9

6:40 pm - 8:05 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 25mnonstop

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

$305Southwest

Sat, Dec 19 - Mon, Dec 21

7:00 am - 9:07 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

8:39 pm - 11:55 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 16mnonstop

$329American Airlines

Sun, Nov 22 - Mon, Nov 23

6:00 am - 7:51 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

6:25 pm - 9:47 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 22mnonstop

$329United Airlines

Sat, Nov 21 - Sun, Nov 22

6:19 pm - 8:20 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

8:10 am - 11:20 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 10mnonstop

$329American Airlines

Tue, Oct 27 - Thu, Oct 29

5:02 pm - 6:50 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

3:00 pm - 6:18 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

$339United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$107

Best time to beat the crowds with an average 46% drop in price.

Most popular time to fly with an average 24% increase in price.

Flight from New Haven 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

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

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$107 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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Flights from domestic origins to Chicago

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Flights to other popular destinations

Find deals for your return flight