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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$68 CHEAP FLIGHTS from Connecticut to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

...and more

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41,299,237 searches in the past 7 days on KAYAK

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Cheapest round-trip

$118

Typical prices: $157-$389

Frontier

Tue 10/28Tue 10/28

JFK - ORD • Non-stop

Cheapest non-stop

$118

Typical prices: $157-$314

Frontier

Wed 11/12Fri 11/14

JFK - ORD • Non-stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

Flight Deals

Cheap Flights from Connecticut to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Connecticut to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

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, Oct 28 - Tue, Oct 28

11:00 am - 12:45 pmJFK-ORD

2h 45mnonstop

6:25 pm - 11:59 amORD-JFK

16h 34m1 stop

$118Frontier

Find Deal

Thu, Nov 13 - Sun, Nov 16

12:59 pm - 2:31 pmLGA-ORD

2h 32mnonstop

7:34 pm - 10:42 pmORD-LGA

2h 08mnonstop

$118Spirit Airlines

Find Deal

Sat, Oct 25 - Sat, Nov 1

7:10 am - 5:53 pmLGA-ORD

11h 43m1 stop

11:51 am - 6:59 pmORD-LGA

6h 08m1 stop

$122Multiple Airlines

Find Deal

Fri, Nov 14 - Mon, Nov 17

8:30 pm - 11:30 amLGA-ORD

16h 00m1 stop

7:34 pm - 10:42 pmORD-LGA

2h 08mnonstop

$126Multiple Airlines

Find Deal

Sat, Nov 1 - Mon, Nov 3

6:45 pm - 8:37 pmJFK-ORD

2h 52mnonstop

6:45 am - 9:59 amORD-JFK

2h 14mnonstop

$133JetBlue

Find Deal

Tue, Oct 28 - Wed, Oct 29

2:30 pm - 4:13 pmJFK-ORD

2h 43mnonstop

1:43 pm - 5:05 pmORD-JFK

2h 22mnonstop

$137American Airlines

Find Deal

Sat, Nov 1 - Tue, Nov 4

8:15 am - 9:40 amLGA-MDW

2h 25mnonstop

7:15 pm - 10:20 pmMDW-LGA

2h 05mnonstop

$137Southwest

Find Deal

Sat, Oct 25 - Tue, Oct 28

4:30 pm - 6:25 pmJFK-ORD

2h 55mnonstop

7:00 am - 10:15 amORD-JFK

2h 15mnonstop

$138JetBlue

Find Deal

Fri, Nov 14 - Mon, Nov 17

9:55 pm - 11:20 pmLGA-MDW

2h 25mnonstop

5:55 pm - 9:00 pmMDW-LGA

2h 05mnonstop

$138Southwest

Find Deal

Thu, Dec 4 - Sun, Dec 7

4:30 pm - 6:23 pmLGA-ORD

2h 53mnonstop

6:22 am - 9:30 amORD-LGA

2h 08mnonstop

$140American Airlines

Find Deal

Useful Info

Low season	January
High season	October
Cheapest flight	$68

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly with an average 3% 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

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

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 $526

Business Class flights to Chicagofrom $510

Prem Econ Class flights to Chicagofrom $580

Economy Class flights to Chicagofrom $92

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

$68 Find Cheap Flights from Connecticut to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Everything you should know

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

FAQs for booking flights from Connecticut to Chicago

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.

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