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>

$43 CHEAP FLIGHTS from Connecticut to Chicago

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

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Flights 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

Sat, Aug 23 - Mon, Aug 25

11:00 am - 1:05 pmJFK-ORD

27h 05m1 stop

6:00 pm - 7:29 amORD-JFK

12h 29m1 stop

$103Frontier

Find Deal

Tue, Aug 19 - Tue, Aug 26

6:00 am - 3:10 pmJFK-ORD

10h 10m1 stop

2:40 pm - 12:27 amORD-JFK

8h 47m1 stop

$105Frontier

Find Deal

Fri, Sep 19 - Sun, Sep 21

3:13 pm - 4:51 pmLGA-ORD

2h 38mnonstop

7:45 am - 4:41 pmORD-LGA

7h 56m1 stop

$116

Find Deal

Tue, Jul 22 - Wed, Jul 23

6:30 am - 4:38 pmLGA-ORD

11h 08m1 stop

5:51 am - 9:00 amORD-LGA

2h 09mnonstop

$118

Find Deal

Wed, Jul 23 - Tue, Jul 29

6:30 pm - 8:00 pmLGA-ORD

2h 30mnonstop

5:51 am - 9:00 amORD-LGA

2h 09mnonstop

$119Spirit Airlines

Find Deal

Tue, Jul 22 - Tue, Jul 29

6:30 pm - 8:00 pmLGA-ORD

2h 30mnonstop

5:51 am - 9:00 amORD-LGA

2h 09mnonstop

$120Spirit Airlines

Find Deal

Thu, Sep 11 - Thu, Sep 11

6:10 am - 7:53 amBDL-ORD

2h 43mnonstop

11:06 am - 2:24 pmORD-BDL

2h 18mnonstop

$132United Airlines

Find Deal

Thu, Sep 4 - Sun, Sep 7

6:10 am - 7:53 amBDL-ORD

2h 43mnonstop

8:48 am - 12:20 pmORD-BDL

2h 32mnonstop

$137United Airlines

Find Deal

Sat, Aug 30 - Tue, Sep 2

9:29 am - 11:18 amJFK-ORD

2h 49mnonstop

11:35 am - 2:58 pmORD-JFK

2h 23mnonstop

$137JetBlue

Find Deal

Tue, Sep 2 - Sat, Sep 6

8:30 pm - 10:28 pmJFK-ORD

2h 58mnonstop

8:34 am - 12:00 pmORD-JFK

2h 26mnonstop

$142JetBlue

Find Deal

Useful Info

Low season	January
High season	July
Cheapest flight	$43

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly and prices are also 0% lower on average.

Flight from New York John F Kennedy 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.

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 $616

Business Class flights to Chicagofrom $608

Prem Econ Class flights to Chicagofrom $557

Economy Class flights to Chicagofrom $51

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

$43 Find Cheap Flights from Connecticut to Chicago

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

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.

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