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>

$59 CHEAP FLIGHTS from Connecticut to Chicago

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

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Cheap Flights from Connecticut to Chicago

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, May 1 - Mon, May 4

10:08 am - 11:42 am

EWR

ORD

2h 34mnonstop

7:33 pm - 8:59 am

ORD

EWR

12h 26m

1 stop

$132Spirit Airlines

Fri, May 1 - Tue, May 12

10:08 am - 11:42 am

EWR

ORD

2h 34mnonstop

5:05 am - 11:52 pm

ORD

EWR

17h 47m

1 stop

$133Spirit Airlines

Thu, Apr 30 - Sat, May 2

1:54 pm - 10:28 am

EWR

MDW

21h 34m

1 stop

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

$134Frontier

Wed, May 6 - Thu, May 7

10:29 pm - 7:55 am

EWR

ORD

10h 26m

1 stop

12:59 pm - 4:06 pm

ORD

EWR

2h 07mnonstop

$135Multiple Airlines

Tue, May 5 - Tue, May 12

6:29 pm - 8:11 pm

LGA

ORD

2h 42mnonstop

1:59 pm - 11:14 pm

ORD

LGA

8h 15m

1 stop

$135Multiple Airlines

Thu, Apr 30 - Sun, May 3

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

$137Frontier

Sat, Jun 6 - Tue, Jun 9

6:00 am - 7:20 am

LGA

MDW

2h 20mnonstop

5:15 am - 8:15 am

MDW

LGA

2h 00mnonstop

$143Southwest

Tue, Jun 9 - Sat, Jun 13

6:00 am - 7:20 am

LGA

MDW

2h 20mnonstop

5:00 am - 8:00 am

MDW

LGA

2h 00mnonstop

$154Southwest

Tue, Jul 7 - Sun, Jul 12

3:30 pm - 5:20 pm

JFK

ORD

2h 50mnonstop

6:00 am - 9:17 am

ORD

JFK

2h 17mnonstop

$172JetBlue

Wed, Jul 1 - Thu, Jul 16

3:30 pm - 5:22 pm

JFK

ORD

2h 52mnonstop

9:39 am - 12:55 pm

ORD

JFK

2h 16mnonstop

$175JetBlue

Useful Info

Low season	January
High season	May
Cheapest flight	$59

Best time to beat the crowds with an average 28% drop in price.

Most popular time to fly with an average 8% 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

Griffith

Saint John

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 $613

Business Class flights to Chicagofrom $548

Premium Economy Class flights to Chicagofrom $426

Economy Class flights to Chicagofrom $102

$59 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