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

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$97

Typical prices: $177-$340

Frontier

Fri 3/6Sun 3/8

JFK - ORD • Non-stop

Cheapest one-way

$53

Overall average: $239

Frontier

Tue 3/17

EWR - MDW • 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, Mar 6 - Sun, Mar 8

4:29 pm - 6:29 pm

JFK

ORD

3h 00mnonstop

12:05 pm - 3:29 pm

ORD

JFK

2h 24mnonstop

$97Frontier

Fri, Feb 27 - Sun, Mar 1

12:59 pm - 9:13 pm

LGA

ORD

9h 14m1 stop

5:58 pm - 8:59 pm

ORD

LGA

2h 01mnonstop

$97Spirit Airlines

Fri, Feb 20 - Fri, Feb 27

11:03 am - 1:03 pm

JFK

ORD

3h 00mnonstop

6:04 am - 9:20 am

ORD

JFK

2h 16mnonstop

$100Multiple Airlines

Fri, Jan 16 - Sun, Jan 18

4:24 pm - 6:24 pm

JFK

ORD

3h 00mnonstop

9:15 am - 12:32 pm

ORD

JFK

2h 17mnonstop

$104Multiple Airlines

Wed, Jan 21 - Thu, Jan 22

11:30 am - 1:15 pm

EWR

ORD

2h 45mnonstop

6:05 am - 9:15 am

ORD

EWR

2h 10mnonstop

$111United Airlines

Tue, Jan 27 - Tue, Jan 27

9:15 am - 10:55 am

LGA

MDW

2h 40mnonstop

2:30 pm - 5:30 pm

MDW

LGA

2h 00mnonstop

$111Southwest

Wed, Feb 11 - Tue, Feb 17

9:15 am - 10:55 am

LGA

MDW

2h 40mnonstop

6:05 pm - 9:10 pm

MDW

LGA

2h 05mnonstop

$120Southwest

Mon, Feb 2 - Wed, Feb 4

12:25 pm - 5:29 pm

JFK

MDW

6h 04m1 stop

6:00 am - 3:14 pm

MDW

JFK

8h 14m1 stop

$157Delta

Sat, Jan 17 - Sat, Jan 17

5:40 am - 9:41 am

BDL

ORD

5h 01m1 stop

2:50 pm - 9:09 pm

ORD

BDL

5h 19m1 stop

$177Delta

Sat, Jan 17 - Tue, Feb 10

4:46 pm - 6:36 pm

BDL

ORD

2h 50mnonstop

11:04 am - 2:22 pm

ORD

BDL

2h 18mnonstop

$185United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$53

Best time to beat the crowds with an average 13% drop in price.

Most popular time to fly with an average 2% increase in price.

Flight from Newark Liberty 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.

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 $466

Business Class flights to Chicagofrom $809

Prem Econ Class flights to Chicagofrom $1,572

Economy Class flights to Chicagofrom $98

$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