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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
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
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 enero 21, 2025.

Round-trip from

$111
(Frontier)

One-way from

$59
(Mytrip)

Good round-trip deal

$392 or less

Good one-way deal

$208 or less
From Connecticut to Chicago (CHI)
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One-way flight from Connecticut to Chicago (CHI)
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Price to beat on a round-trip flight from Connecticut to Chicago (CHI).
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Price to beat on a 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 enero 21, 2025.

This Frontier deal was found by Cheapflights users on 1/21. 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.
lun. 4/286:00 amJFK - ORD
1 stop7h 06mFrontier
mié. 4/3011:57 amORD - JFK
1 stop11h 36mFrontier
Deal found 1/21$111
This Frontier deal was found by Cheapflights users on 1/21. 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.
lun. 4/286:30 amLGA - ORD
1 stop6h 36mFrontier
mié. 4/3011:57 amORD - LGA
1 stop10h 06mFrontier
Deal found 1/21$111
This FlightHub deal was found by Cheapflights users on 1/20. 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.
vie. 3/74:40 pmLGA - ORD
Nonstop2h 46mSpirit Airlines
dom. 3/165:55 amORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 1/20$113
This Frontier deal was found by Cheapflights users on 1/21. 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.
sáb. 4/191:00 pmJFK - MDW
1 stop9h 52mFrontier
lun. 4/216:44 pmMDW - JFK
1 stop11h 43mFrontier
Deal found 1/21$114
This Booking.com deal was found by Cheapflights users on 1/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/610:59 amLGA - ORD
1 stop12h 28mMultiple Airlines
sáb. 2/85:06 pmORD - LGA
Nonstop2h 04mMultiple Airlines
Deal found 1/21$114
This Trip.com deal was found by Cheapflights users on 1/20. 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.
mié. 2/1210:00 pmLGA - MDW
1 stop14h 28mFrontier
mar. 2/188:30 amMDW - LGA
1 stop24h 30mFrontier
Deal found 1/20$114
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 1/245:45 amEWR - ORD
1 stop11h 25mSpirit Airlines
jue. 1/305:50 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 1/21$126
This CheapOair deal was found by Cheapflights users on 1/21. 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.
lun. 2/35:45 amEWR - ORD
1 stop11h 25mMultiple Airlines
mié. 2/51:45 pmORD - EWR
1 stop6h 25mMultiple Airlines
Deal found 1/21$129
This Frontier deal was found by Cheapflights users on 1/21. 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.
mar. 4/1510:00 pmEWR - ORD
1 stop10h 45mFrontier
mar. 4/2211:57 amORD - EWR
1 stop8h 08mFrontier
Deal found 1/21$132
This Delta deal was found by Cheapflights users on 1/21. 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.
jue. 2/133:55 pmJFK - ORD
Nonstop2h 52mDelta
dom. 2/167:05 amORD - JFK
Nonstop2h 22mDelta
Deal found 1/21$147
This American Airlines deal was found by Cheapflights users on 1/20. 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.
mar. 2/113:00 pmEWR - ORD
Nonstop2h 40mAmerican Airlines
dom. 2/166:45 pmORD - EWR
Nonstop2h 12mAmerican Airlines
Deal found 1/20$147
This Delta deal was found by Cheapflights users on 1/21. 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.
jue. 2/137:30 amLGA - ORD
Nonstop2h 48mDelta
mar. 2/187:40 pmORD - LGA
Nonstop2h 20mDelta
Deal found 1/21$147

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

lun. 4/28

6:30 am-12:06 pm

1 stop6h 36m

Chicago O'Hare Intl

mié. 4/30

11:57 am-11:03 pm

1 stop10h 06m

$111

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 2/6

10:59 am-6:26 pm

1 stop8h 27m

Chicago Midway

mié. 2/12

6:00 am-8:59 pm

1 stop13h 59m

$112

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

vie. 3/7

4:40 pm-6:26 pm

Nonstop2h 46m

Chicago O'Hare Intl

dom. 3/16

5:55 am-9:00 am

Nonstop2h 05m

$113

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 2/26

5:59 pm-7:09 am

1 stop14h 10m

Chicago O'Hare Intl

lun. 3/3

5:44 pm-8:29 pm

Nonstop1h 45m

$114

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

sáb. 4/19

1:00 pm-9:52 pm

1 stop9h 52m

Chicago Midway

mar. 4/22

3:20 pm-12:33 am

1 stop8h 13m

$114

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

sáb. 2/1

3:00 pm-9:52 am

1 stop19h 52m

Chicago O'Hare Intl

lun. 2/3

5:28 pm-1:59 pm

1 stop19h 31m

$115

NewarkChicago

EWR - ORD

EWRORD

Newark

lun. 2/3

5:45 am-4:10 pm

1 stop11h 25m

Chicago O'Hare Intl

mié. 2/5

1:45 pm-9:10 pm

1 stop6h 25m

$129

NewarkChicago

EWR - ORD

EWRORD

Newark

jue. 2/13

6:59 pm-5:28 am

1 stop11h 29m

Chicago O'Hare Intl

jue. 2/20

5:15 am-8:24 am

Nonstop2h 09m

$134

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mar. 2/11

3:55 pm-5:47 pm

Nonstop2h 52m

Chicago O'Hare Intl

vie. 2/14

6:30 pm-10:02 pm

Nonstop2h 32m

$145

NewarkChicago

EWR - ORD

EWRORD

Newark

mar. 2/11

3:00 pm-4:40 pm

Nonstop2h 40m

Chicago O'Hare Intl

sáb. 2/15

5:59 pm-8:57 pm

Nonstop1h 58m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 60 results
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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 enero 21, 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 enero 21, 2025.

The most flights from USCT to CHI are scheduled on a Tuesday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated enero 21, 2025.
Peruse reviews from past customers who have flown with American Airlines, JetBlue and United Airlines from Connecticut to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,985 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $59. Users have also found prices from $60 and $74 on Spirit Airlines and JetBlue, respectively.

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

    The most popular route from Connecticut to Chicago is New York John F Kennedy Intl - Chicago O'Hare Intl. You may also consider New York LaGuardia - Chicago O'Hare Intl or Newark - 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: Japan Airlines (90%), Republic Airways (87%), ANA( 86%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $1,151 for a flight from Connecticut to Chicago. The cheapest flight overall is $164 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $126.

  • 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, 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.

See more FAQs

Traveling to a place near Connecticut?

Book flights to Connecticut if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.
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Top 7 airlines flying from Connecticut to Chicago

Discover the top 7 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$204FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$225FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$117Average$225FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$296FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$197Average$340FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$401FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$232Average$364FlexibilityNo cancel feeOn-time63%
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