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>

$53 CHEAP FLIGHTS from Connecticut to Chicago

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

...and more

Travelers love KAYAK

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

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Cheapest round-trip

$84

Overall average: $177

Multiple Airlines

Fri 1/30Tue 2/3

JFK - ORD • Non-stop

Cheapest one-way

$53

Typical prices: $73-$218

Spirit Airlines

Wed 1/21

LGA - 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

Fri, Jan 30 - Tue, Feb 3

4:29 pm - 6:29 pmJFK-ORD

3h 00mnonstop

9:40 am - 12:56 pmORD-JFK

2h 16mnonstop

$84Multiple Airlines

Find Deal

Wed, Jan 14 - Sat, Jan 17

4:24 pm - 6:24 pmJFK-ORD

3h 00mnonstop

12:00 pm - 3:24 pmORD-JFK

2h 24mnonstop

$85Frontier

Find Deal

Sat, Dec 13 - Mon, Dec 15

8:41 pm - 10:11 pmLGA-ORD

2h 30mnonstop

4:38 pm - 7:42 pmORD-LGA

2h 04mnonstop

$86Spirit Airlines

Find Deal

Sat, Dec 13 - Mon, Dec 15

8:41 pm - 10:11 pmLGA-ORD

2h 30mnonstop

4:38 pm - 7:42 pmORD-LGA

2h 04mnonstop

$87Spirit Airlines

Find Deal

Wed, Jan 14 - Sat, Jan 17

7:30 am - 9:12 amLGA-ORD

2h 42mnonstop

5:53 pm - 8:59 pmORD-LGA

2h 06mnonstop

$90Spirit Airlines

Find Deal

Fri, Dec 12 - Fri, Dec 19

1:00 pm - 2:57 pmJFK-ORD

2h 57mnonstop

6:40 am - 10:04 amORD-JFK

2h 24mnonstop

$91Frontier

Find Deal

Wed, Feb 11 - Wed, Feb 11

6:00 am - 7:40 amLGA-MDW

2h 40mnonstop

7:15 pm - 10:20 pmMDW-LGA

2h 05mnonstop

$103Southwest

Find Deal

Wed, Jan 7 - Wed, Jan 7

6:00 am - 7:40 amLGA-MDW

2h 40mnonstop

12:50 pm - 3:50 pmMDW-LGA

2h 00mnonstop

$109Southwest

Find Deal

Thu, Jan 22 - Sat, Jan 24

7:20 am - 11:59 amBDL-MDW

5h 39m1 stop

11:45 am - 8:09 pmMDW-BDL

7h 24m1 stop

$177Delta

Find Deal

Thu, Jan 15 - Wed, Jan 21

5:40 am - 9:41 amBDL-ORD

5h 01m1 stop

6:15 am - 1:45 pmORD-BDL

6h 30m1 stop

$177Delta

Find Deal

Useful Info

Low season	January
High season	November
Cheapest flight	$53

Best time to beat the crowds with an average 14% drop in price.

Most popular time to fly with an average 12% increase in price.

Flight from New York LaGuardia 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

Chesterton

Schererville

Munster

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 $650

Business Class flights to Chicagofrom $635

Prem Econ Class flights to Chicagofrom $1,046

Economy Class flights to Chicagofrom $95

$53 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