$43 Find Cheap Flights from Connecticut to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 8/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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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.

Recent round-trip flight deals from Connecticut to Chicago

Sat, Aug 23 - Mon, Aug 25
Frontier Logo
11:00 am - 1:05 pmJFK-ORD
27h 05m1 stop
Frontier Logo
6:00 pm - 7:29 amORD-JFK
12h 29m1 stop
$103Frontier
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Tue, Aug 19 - Tue, Aug 26
Frontier Logo
6:00 am - 3:10 pmJFK-ORD
10h 10m1 stop
Frontier Logo
2:40 pm - 12:27 amORD-JFK
8h 47m1 stop
$105Frontier
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Fri, Sep 19 - Sun, Sep 21
 Logo
3:13 pm - 4:51 pmLGA-ORD
2h 38mnonstop
 Logo
7:45 am - 4:41 pmORD-LGA
7h 56m1 stop
Tue, Jul 22 - Wed, Jul 23
 Logo
6:30 am - 4:38 pmLGA-ORD
11h 08m1 stop
 Logo
5:51 am - 9:00 amORD-LGA
2h 09mnonstop
Wed, Jul 23 - Tue, Jul 29
Spirit Airlines Logo
6:30 pm - 8:00 pmLGA-ORD
2h 30mnonstop
Spirit Airlines Logo
5:51 am - 9:00 amORD-LGA
2h 09mnonstop
$119Spirit Airlines
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Tue, Jul 22 - Tue, Jul 29
Spirit Airlines Logo
6:30 pm - 8:00 pmLGA-ORD
2h 30mnonstop
Spirit Airlines Logo
5:51 am - 9:00 amORD-LGA
2h 09mnonstop
$120Spirit Airlines
Find Deal
Thu, Sep 11 - Thu, Sep 11
United Airlines Logo
6:10 am - 7:53 amBDL-ORD
2h 43mnonstop
United Airlines Logo
11:06 am - 2:24 pmORD-BDL
2h 18mnonstop
$132United Airlines
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Thu, Sep 4 - Sun, Sep 7
United Airlines Logo
6:10 am - 7:53 amBDL-ORD
2h 43mnonstop
United Airlines Logo
8:48 am - 12:20 pmORD-BDL
2h 32mnonstop
$137United Airlines
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Sat, Aug 30 - Tue, Sep 2
JetBlue Logo
9:29 am - 11:18 amJFK-ORD
2h 49mnonstop
JetBlue Logo
11:35 am - 2:58 pmORD-JFK
2h 23mnonstop
$137JetBlue
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Tue, Sep 2 - Sat, Sep 6
JetBlue Logo
8:30 pm - 10:28 pmJFK-ORD
2h 58mnonstop
JetBlue Logo
8:34 am - 12:00 pmORD-JFK
2h 26mnonstop
$142JetBlue
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Good to know

Low seasonJanuary
High seasonJuly
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

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

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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