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$96+ Cheap flights from Connecticut to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Aug 2 — Aug 91
Sun 8/2
Sun 8/9
1 adult, Economy
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Cheap flight deals from Connecticut to Chicago

Cheapest flights from Connecticut to Chicago
Explore the most affordable flight options available from Connecticut to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:00 pm
JFK
-
ORD
Nonstop2h 58m
JetBlue
Wed 8/196:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Deal found 6/30$191
This American Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:29 pm
LGA
-
ORD
Nonstop3h 01m
American Airlines
Tue 9/88:25 pm
ORD
-
LGA
Nonstop2h 20m
American Airlines
Deal found 6/29$191
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:33 am
JFK
-
ORD
Nonstop2h 54m
Delta
Tue 9/86:00 am
ORD
-
JFK
Nonstop2h 21m
Delta
Deal found 7/3$192
This Super.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:40 pm
JFK
-
ORD
Nonstop2h 55m
JetBlue
Thu 9/101:00 pm
ORD
-
JFK
Nonstop2h 20m
JetBlue
Deal found 7/3$193
This JetBlue deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:05 am
JFK
-
ORD
Nonstop2h 46m
JetBlue
Wed 7/226:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Deal found 7/1$194
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:55 pm
LGA
-
ORD
Nonstop3h 04m
Delta
Wed 7/227:00 am
ORD
-
LGA
Nonstop2h 14m
Delta
Deal found 7/1$194
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:35 pm
LGA
-
MDW
Nonstop2h 50m
Southwest
Wed 7/227:45 pm
MDW
-
LGA
Nonstop2h 15m
Southwest
Deal found 7/1$194
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:55 am
JFK
-
ORD
Nonstop2h 48m
JetBlue
Sat 8/225:27 pm
ORD
-
JFK
Nonstop2h 33m
JetBlue
Deal found 7/3$195
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:00 pm
LGA
-
ORD
Nonstop3h 03m
Delta
Tue 8/256:00 am
ORD
-
LGA
Nonstop2h 09m
Delta
Deal found 7/3$195
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Thu 8/612:50 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 7/3$195
This Cheapflightsfares deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:05 am
JFK
-
ORD
Nonstop2h 45m
JetBlue
Tue 7/216:30 pm
ORD
-
JFK
Nonstop2h 36m
JetBlue
Deal found 6/30$196
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:16 am
LGA
-
ORD
Nonstop2h 49m
American Airlines
Wed 8/198:25 pm
ORD
-
LGA
Nonstop2h 20m
American Airlines
Deal found 7/3$196

Find flight deals from Connecticut to Chicago

Keep the following information in mind while searching for Connecticut to Chicago flight deals. Data was last updated July 3, 2026.

Round-trip from

$191
(Cheapflightsfares)

One-way from

$96
(Super.com)

Popular in

June

Cheapest in

January

Average price

$430

Good round-trip deal

$282 or less

Good one-way deal

$74 or less
From Connecticut to Chicago (CHI)
Search Deals
One-way flight from Connecticut to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Connecticut to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Connecticut to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2026.
Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 7/18

9:10 pm-10:50 pm

Nonstop2h 40m

Chicago Midway

Wed 7/22

7:45 pm-11:00 pm

Nonstop2h 15m

$194

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 8/20

6:00 am-9:38 am

1 stop4h 38m

Chicago O'Hare Intl

Tue 9/1

6:29 pm-9:54 pm

Nonstop2h 25m

$197

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 7/27

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Wed 7/29

7:45 pm-11:00 pm

Nonstop2h 15m

$199

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 8/20

11:25 am-1:00 pm

Nonstop2h 35m

Chicago O'Hare Intl

Mon 8/31

7:05 pm-10:34 pm

Nonstop2h 29m

$203

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 8/3

6:00 am-7:29 am

Nonstop2h 29m

Chicago O'Hare Intl

Thu 8/6

6:00 am-9:09 am

Nonstop2h 09m

$205

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 10/1

2:50 pm-4:30 pm

Nonstop2h 40m

Chicago O'Hare Intl

Sun 10/4

7:00 am-10:15 am

Nonstop2h 15m

$205
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 8/13

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Sun 8/16

5:25 am-8:25 am

Nonstop2h 00m

$205

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 8/23

6:10 am-7:50 am

Nonstop2h 40m

Chicago O'Hare Intl

Fri 8/28

4:59 pm-8:24 pm

Nonstop2h 25m

$207

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 9/4

8:55 pm-10:15 pm

Nonstop2h 20m

Chicago Midway

Sun 9/6

8:45 am-11:55 am

Nonstop2h 10m

$207

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 9/21

6:00 am-9:38 am

1 stop4h 38m

Chicago O'Hare Intl

Thu 9/24

12:00 pm-3:17 pm

Nonstop2h 17m

$213

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Connecticut to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Connecticut with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Connecticut to Chicago

What is the cheapest month to book a flight from Connecticut to Chicago?

Currently, November is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $55). Flying from Connecticut to Chicago in June is currently the most expensive (average of $161). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CT to CHI?

Find hourly flight availability from Connecticut to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 22% on flights from Connecticut to Chicago by exploring options for tickets in the afternoon.

Weekly flight availability from Connecticut to Chicago

Explore weekly flight availability from Connecticut to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 3, 2026.

The most flights from USCT to CHI are scheduled on a Thursday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

How much does it cost to fly round-trip from Connecticut to Chicago?

How far ahead should I book a flight from Connecticut to Chicago?

The best time to book flights from Connecticut to Chicago is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest day to fly from Connecticut to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Connecticut to Chicago. Price data was last updated on June 27, 2026.

Travelers seeking maximum savings on their Connecticut to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Connecticut to Chicago?

    A quick flight from Connecticut to Chicago can take about 2h 35m. Southwest provides one of the quickest options available for as low as $203. Airlines will cover a distance of 731 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Connecticut to Chicago one-way?

    For one-way options, check prices for Avelo Airlines. According to our data, you can fly for as low as $37. Users have also found prices from $68 and $78 on Southwest and American Airlines, respectively.

  • What are the most popular routes from Connecticut to Chicago?

    The most popular route from Connecticut to Chicago is Newark - Chicago O'Hare Intl. You may also consider New York John F Kennedy Intl - Chicago O'Hare Intl or New York LaGuardia - Chicago O'Hare Intl.

  • What are the most reliable airlines from Connecticut to Chicago?

    Before booking your flight to Chicago from Connecticut, check out the most reliable airlines to get you to your destination on time: ANA (89%), Copa Airlines (87%), Air New Zealand( 87%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $997 for a flight from Connecticut to Chicago. The cheapest flight overall is $164 while the most popular route, (Newark - Chicago O'Hare Intl) is currently priced at $171.

  • Can I find deals for flights from Connecticut to Chicago that include hotel bookings?

    Yes. In addition to deals on Connecticut to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Chicago.

  • Can I find deals for business class flights from Connecticut to Chicago?

    Yes. Cheapflights offers flight deals from Connecticut to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Connecticut to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $55). Flying from Connecticut to Chicago in June is currently the most expensive (average of $161). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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Alternative routes for Connecticut to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
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Dallas/Fort Worth to Midway flights
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Newark to Midway flights
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Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Ontario to O'Hare Intl flights
Boston to O'Hare Intl flights
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George Bush Intcntl to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
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Tampa to O'Hare Intl flights
Los Angeles to Midway flights
Fort Lauderdale to O'Hare Intl flights
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San Diego to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Miami to O'Hare Intl flights
Dulles Intl to Midway flights
Santa Ana to O'Hare Intl flights
Atlanta to Midway flights
San Francisco to Midway flights
LaGuardia to St. Louis flights
John F Kennedy Intl to Midway flights
LaGuardia to Midway flights
Baltimore to Midway flights
Minneapolis to Midway flights
Minneapolis to O'Hare Intl flights
Portland to O'Hare Intl flights
Hobby to Midway flights
San Jose to O'Hare Intl flights
Philadelphia to Midway flights
Sacramento to O'Hare Intl flights
New Orleans to O'Hare Intl flights
Reagan-National to Midway flights
Las Vegas to O'Hare Intl flights
Burbank to O'Hare Intl flights
Seattle to Midway flights

Top 6 airlines flying from Connecticut to Chicago

Discover the top 6 airlines that operate flights from Connecticut to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$215FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$84Average$206FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$246FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$177Average$387FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$199Average$412FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$225Average$433FlexibilityNo cancel feeOn-time69%

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