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>

$23 CHEAP FLIGHTS from Connecticut to Chicago

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

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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

sáb., sep. 13 - sáb., sep. 20

8:36 pm - 10:11 pmLGA-ORD

2h 35mnonstop

4:35 pm - 7:41 pmORD-LGA

2h 06mnonstop

$47Spirit Airlines

Find Deal

sáb., sep. 6 - mar., sep. 16

3:12 pm - 4:50 pmLGA-ORD

2h 38mnonstop

11:13 am - 2:18 pmORD-LGA

2h 05mnonstop

$49Spirit Airlines

Find Deal

vie., oct. 24 - lun., oct. 27

11:00 am - 12:45 pmJFK-ORD

2h 45mnonstop

6:40 am - 10:03 amORD-JFK

2h 23mnonstop

$73Frontier

Find Deal

vie., oct. 17 - lun., oct. 20

11:00 am - 12:45 pmJFK-ORD

2h 45mnonstop

6:40 am - 10:03 amORD-JFK

2h 23mnonstop

$74Frontier

Find Deal

sáb., sep. 13 - lun., sep. 15

8:36 pm - 10:11 pmLGA-ORD

2h 35mnonstop

10:25 am - 11:57 pmORD-LGA

12h 32m1 stop

$102

Find Deal

lun., sep. 8 - mié., sep. 10

6:30 am - 3:50 pmLGA-ORD

10h 20m1 stop

10:27 am - 11:03 pmORD-LGA

11h 36m1 stop

$120

Find Deal

mar., sep. 16 - mar., sep. 16

6:10 am - 7:53 amBDL-ORD

2h 43mnonstop

11:06 am - 2:24 pmORD-BDL

2h 18mnonstop

$132United Airlines

Find Deal

mié., sep. 3 - jue., sep. 4

8:15 pm - 9:56 pmEWR-ORD

2h 41mnonstop

9:08 pm - 12:30 amORD-EWR

2h 22mnonstop

$137United Airlines

Find Deal

sáb., ago. 30 - lun., sep. 1

8:30 pm - 10:28 pmJFK-ORD

2h 58mnonstop

6:15 am - 9:27 amORD-JFK

2h 12mnonstop

$137JetBlue

Find Deal

sáb., sep. 27 - sáb., oct. 4

4:30 pm - 6:23 pmJFK-ORD

2h 53mnonstop

8:34 am - 12:04 pmORD-JFK

2h 30mnonstop

$145JetBlue

Find Deal

Useful Info

Low season	January
High season	October
Cheapest flight	$23

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

Most popular time to fly and prices are also 3% lower on average.

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

Valparaiso

Lansing

Chesterton

Munster

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 $419

Business Class flights to Chicagofrom $463

Prem Econ Class flights to Chicagofrom $572

Economy Class flights to Chicagofrom $93

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

$23 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.

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