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$55+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Jan 20 — Jan 271
Mon 1/20
Mon 1/27
1 adult, Economy
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Cheap flight deals from Connecticut to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Connecticut (USCT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 15, 2025.

Round-trip from

$116
(Cheapflightsfares)

One-way from

$55
(Frontier)
From Connecticut to Chicago (CHI)
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One-way flight from Connecticut to Chicago (CHI)
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Find 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 January 15, 2025.

This Flightnetwork deal was found by Cheapflights users on 1/15. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/239:59 amLGA - ORD
1 stop11h 14mSpirit Airlines
Mon 1/277:00 amORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 1/15$116
This Delta deal was found by Cheapflights users on 1/14. 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 2/63:55 pmJFK - ORD
Nonstop2h 52mDelta
Mon 2/1010:05 amORD - JFK
Nonstop2h 24mDelta
Deal found 1/14$117
This Trip.com deal was found by Cheapflights users on 1/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/411:00 amJFK - MDW
1 stop6h 16mFrontier
Wed 2/124:20 pmMDW - JFK
1 stop16h 55mFrontier
Deal found 1/15$117
This United Airlines deal was found by Cheapflights users on 1/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/185:16 pmLGA - ORD
Nonstop2h 39mUnited Airlines
Tue 1/218:00 pmORD - LGA
Nonstop2h 17mUnited Airlines
Deal found 1/14$117
This Southwest deal was found by Cheapflights users on 1/14. 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.
Thu 2/66:00 amLGA - MDW
Nonstop2h 35mSouthwest
Mon 2/106:00 amMDW - LGA
Nonstop2h 10mSouthwest
Deal found 1/14$117
This JetBlue deal was found by Cheapflights users on 1/14. 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 1/231:50 pmJFK - ORD
Nonstop2h 54mJetBlue
Mon 1/275:05 pmORD - JFK
Nonstop2h 26mJetBlue
Deal found 1/14$118
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Thu 2/610:18 amLGA - ORD
Nonstop2h 48mAmerican Airlines
Mon 2/1012:20 pmORD - LGA
Nonstop2h 07mAmerican Airlines
Deal found 1/14$118
This FlightHub deal was found by Cheapflights users on 1/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1011:01 amJFK - ORD
1 stop6h 30mFrontier
Tue 3/1112:02 pmORD - JFK
1 stop21h 13mFrontier
Deal found 1/14$119
This CheapOair deal was found by Cheapflights users on 1/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/210:59 amLGA - ORD
Nonstop2h 40mMultiple Airlines
Mon 2/38:38 amORD - LGA
1 stop5h 32mMultiple Airlines
Deal found 1/14$119
This Frontier deal was found by Cheapflights users on 1/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/3110:59 amLGA - ORD
1 stop10h 58mFrontier
Mon 2/38:38 amORD - LGA
1 stop5h 32mFrontier
Deal found 1/14$120
This Frontier deal was found by Cheapflights users on 1/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/3010:59 amLGA - MDW
1 stop8h 27mFrontier
Fri 1/316:40 amMDW - LGA
1 stop7h 30mFrontier
Deal found 1/14$120
This Frontier deal was found by Cheapflights users on 1/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2010:20 pmEWR - ORD
1 stop10h 28mFrontier
Mon 2/248:23 amORD - EWR
1 stop11h 47mFrontier
Deal found 1/14$133

Find flights from Connecticut to Chicago within your budget

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 January 15, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 3/14

4:40 pm-6:26 pm

Nonstop2h 46m

Chicago O'Hare Intl

Sun 3/16

5:55 am-9:00 am

Nonstop2h 05m

$116

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/6

3:55 pm-5:47 pm

Nonstop2h 52m

Chicago O'Hare Intl

Tue 2/11

10:05 am-1:29 pm

Nonstop2h 24m

$117

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 2/4

11:00 am-4:16 pm

1 stop6h 16m

Chicago Midway

Wed 2/12

4:20 pm-10:15 am

1 stop16h 55m

$117

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 2/6

6:00 am-7:35 am

Nonstop2h 35m

Chicago Midway

Mon 2/10

6:00 am-9:10 am

Nonstop2h 10m

$117

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/6

1:50 pm-3:43 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 2/10

5:05 pm-8:30 pm

Nonstop2h 25m

$118

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 2/2

9:15 pm-10:55 pm

Nonstop2h 40m

Chicago O'Hare Intl

Mon 2/3

8:38 am-3:10 pm

1 stop5h 32m

$119

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 3/10

11:01 am-4:31 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 3/11

12:02 pm-10:15 am

1 stop21h 13m

$119

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 1/31

10:59 am-8:57 pm

1 stop10h 58m

Chicago O'Hare Intl

Mon 2/3

8:38 am-3:10 pm

1 stop5h 32m

$120

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/30

10:59 am-6:26 pm

1 stop8h 27m

Chicago Midway

Fri 1/31

6:40 am-3:10 pm

1 stop7h 30m

$120

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 2/20

10:20 pm-7:48 am

1 stop10h 28m

Chicago O'Hare Intl

Mon 2/24

8:23 am-9:10 pm

1 stop11h 47m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

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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.

Travel insights for flights from Connecticut to Chicago

Get recent, data-driven insights about flights from Connecticut to Chicago including ideal travel times, pricing trends, and more.

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

Currently, August is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $245). Flying from Connecticut to Chicago in March is currently the most expensive (average of $320). 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 January 15, 2025.

When flying from Connecticut to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 January 15, 2025.