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.

$75 CHEAP FLIGHTS from Connecticut to Chicago

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Cheap Flights from Connecticut to Chicago

Cheap flights from Connecticut to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Thu, Nov 5 - Mon, Nov 9

4:45 pm - 6:24 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

$164Avelo Airlines

Thu, Nov 5 - Mon, Nov 9

4:45 pm - 6:24 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

$164Avelo Airlines

Thu, Nov 5 - Mon, Nov 9

7:00 pm - 8:46 amHVN Tweed-New Haven-ORD Chicago O'Hare Intl

14h 46m2 stops Baltimore/Washington Orlando

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

2h 22mnonstop

$267Multiple Airlines

Thu, Nov 5 - Mon, Nov 9

8:50 am - 6:45 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

10h 55m1 stop Atlanta Hartsfield-Jackson

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

2h 22mnonstop

$267Multiple Airlines

Wed, Oct 28 - Fri, Oct 30

10:37 am - 4:37 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

7h 00m1 stop Washington, D.C. Dulles Intl

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

2h 22mnonstop

$302United Airlines

Tue, Nov 3 - Fri, Nov 6

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

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

2:36 pm - 5:54 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

$302United Airlines

Tue, Nov 17 - Sun, Nov 22

12:30 pm - 6:55 pmBDL Hartford Bradley Intl-MDW Chicago Midway

7h 25m1 stop Baltimore/Washington

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

2h 10mnonstop

$303Southwest

Wed, Dec 16 - Sat, Dec 19

7:45 am - 9:15 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

5:25 am - 12:00 pmMDW Chicago Midway-BDL Hartford Bradley Intl

5h 35m1 stop Baltimore/Washington

$303Southwest

Wed, Dec 16 - Sat, Dec 19

6:14 pm - 8:21 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

6:45 am - 1:25 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

5h 40m1 stop Philadelphia

$303American Airlines

Thu, Nov 19 - Sun, Nov 22

5:30 am - 10:15 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

5h 45m1 stop Washington, D.C. Reagan-National

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

2h 10mnonstop

$304American Airlines

Thu, Oct 15 - Mon, Oct 19

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

$249Avelo Airlines

Fri, Oct 16 - Mon, Oct 19

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

$259Avelo Airlines

Sun, Oct 18 - Thu, Nov 12

3:16 pm - 7:31 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

17h 15m1 stop Orlando

7:50 pm - 11:44 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

26h 54m2 stops Atlanta Hartsfield-Jackson Jacksonville

$371Multiple Airlines

Sat, Oct 17 - Thu, Oct 22

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

Sun, Oct 18 - Thu, Nov 12

3:16 pm - 7:02 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

28h 46m1 stop Orlando

9:51 am - 2:20 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

27h 29m1 stop Orlando

$385Frontier

Sat, Oct 17 - Tue, Oct 20

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

$415JetBlue

Sun, Oct 18 - Thu, Nov 12

6:05 am - 7:50 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 45mnonstop

7:25 am - 10:43 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

$415United Airlines

Sun, Oct 18 - Thu, Nov 12

6:00 am - 9:38 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

4h 38m1 stop Washington, D.C. Dulles Intl

2:36 pm - 5:54 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

$425United Airlines

Wed, Oct 14 - Sat, Oct 17

1:00 pm - 2:48 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

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

2h 21mnonstop

$477American Airlines

Sat, Oct 17 - Tue, Oct 20

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

3h 21mnonstop

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

2h 25mnonstop

$477American Airlines

Thu, Nov 5 - Mon, Nov 9

4:45 pm - 6:24 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

$164Avelo Airlines

Thu, Nov 5 - Mon, Nov 9

4:45 pm - 6:24 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

$164Avelo Airlines

Fri, Nov 6 - 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

$169Avelo Airlines

Mon, Oct 26 - Fri, Oct 30

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

2h 51mnonstop

11:04 am - 2:19 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 15mnonstop

$310United Airlines

Sat, Oct 31 - Mon, Nov 2

12:40 pm - 2:32 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

11:00 am - 2:18 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

$313United Airlines

Sat, Oct 31 - Tue, Nov 3

12:32 pm - 2:20 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

8:30 pm - 11:48 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

$313American Airlines

Fri, Oct 30 - Thu, Nov 5

1:00 pm - 2:48 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

8:10 am - 11:25 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 15mnonstop

$313American Airlines

Fri, Oct 30 - Thu, Nov 5

12:30 pm - 1:50 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

7:10 pm - 10:15 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

$313Southwest

Tue, Nov 17 - Thu, Nov 19

6:25 pm - 7:55 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

6:20 pm - 9:25 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

$313Southwest

Wed, Dec 23 - Wed, Dec 30

6:44 pm - 8:40 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

10:45 am - 2:08 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 23mnonstop

$329United Airlines

Low season	January
High season	July
Cheapest flight	$75

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

Most popular time to fly with an average 23% 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.