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$60+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheap flight deals from Connecticut to Chicago

Keep the following information in mind while searching for Connecticut to Chicago flight deals. Data was last updated April 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$118
(Cheapflightsfares)

One-way from

$60
(Kiwi.com)

Good round-trip deal

$366 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for Springfield (SFY)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Springfield (SFY)-Chicago (CHI) flights.
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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 April 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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.
Sat 6/145:00 amEWR - ORD
Nonstop2h 37mSpirit Airlines
Thu 6/199:28 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 4/28$118
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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.
Fri 5/3011:55 amLGA - ORD
1 stop12h 34mSpirit Airlines
Mon 6/27:35 pmORD - LGA
1 stop13h 25mSpirit Airlines
Deal found 4/27$138
This Delta deal was found by Cheapflights users on 4/28. 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.
Tue 5/1311:00 amJFK - ORD
Nonstop2h 48mDelta
Wed 5/2110:31 amORD - JFK
Nonstop2h 19mDelta
Deal found 4/28$147
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/248:30 pmEWR - ORD
Nonstop2h 42mUnited Airlines
Sun 5/256:00 amORD - EWR
Nonstop2h 13mUnited Airlines
Deal found 4/28$147
This JetBlue deal was found by Cheapflights users on 4/28. 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.
Mon 5/198:00 pmJFK - ORD
Nonstop2h 54mJetBlue
Tue 5/276:15 amORD - JFK
Nonstop2h 15mJetBlue
Deal found 4/28$153
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 5/2011:25 amLGA - ORD
Nonstop2h 41mUnited Airlines
Tue 5/206:30 pmORD - LGA
Nonstop2h 18mUnited Airlines
Deal found 4/28$157
This Southwest deal was found by Cheapflights users on 4/28. 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 5/286:10 amLGA - MDW
Nonstop2h 20mSouthwest
Wed 6/48:20 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 4/28$157
This Delta deal was found by Cheapflights users on 4/28. 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.
Tue 5/202:45 pmLGA - ORD
Nonstop2h 43mDelta
Wed 5/217:00 amORD - LGA
Nonstop2h 12mDelta
Deal found 4/28$169
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Sat 6/215:45 amLGA - ORD
Nonstop2h 42mAmerican Airlines
Wed 6/258:25 pmORD - LGA
Nonstop2h 20mAmerican Airlines
Deal found 4/29$178
This Delta deal was found by Cheapflights users on 4/28. 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 6/146:00 amEWR - MDW
1 stop3h 41mDelta
Sat 6/215:53 pmMDW - EWR
1 stop4h 07mDelta
Deal found 4/28$179
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 6/45:59 amEWR - ORD
1 stop5h 04mDelta
Sat 6/74:25 pmORD - EWR
1 stop5h 35mDelta
Deal found 4/28$179
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 5/279:00 amJFK - ORD
Nonstop3h 09mAmerican Airlines
Thu 5/294:44 pmORD - JFK
Nonstop2h 16mAmerican Airlines
Deal found 4/29$183

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 April 30, 2025.
Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.

Fly from

Connecticut

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 6/14

5:00 am-6:37 am

Nonstop2h 37m

Chicago O'Hare Intl

Thu 6/19

9:28 pm-12:46 am

Nonstop2h 18m

$118

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 5/30

11:55 am-11:29 pm

1 stop12h 34m

Chicago O'Hare Intl

Mon 6/2

7:35 pm-10:00 am

1 stop13h 25m

$138

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 5/13

11:00 am-12:48 pm

Nonstop2h 48m

Chicago O'Hare Intl

Wed 5/21

10:31 am-1:50 pm

Nonstop2h 19m

$147

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 5/24

8:30 pm-10:12 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sun 5/25

6:00 am-9:13 am

Nonstop2h 13m

$147

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 5/19

8:00 pm-9:54 pm

Nonstop2h 54m

Chicago O'Hare Intl

Tue 5/27

6:15 am-9:30 am

Nonstop2h 15m

$153

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/28

9:45 pm-11:00 pm

Nonstop2h 15m

Chicago Midway

Wed 6/4

8:20 pm-11:25 pm

Nonstop2h 05m

$157

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 5/20

10:25 am-12:05 pm

Nonstop2h 40m

Chicago O'Hare Intl

Wed 5/21

9:00 am-12:13 pm

Nonstop2h 13m

$157

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 5/20

2:45 pm-4:28 pm

Nonstop2h 43m

Chicago O'Hare Intl

Wed 5/21

7:00 am-10:12 am

Nonstop2h 12m

$169

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 6/21

5:45 am-7:27 am

Nonstop2h 42m

Chicago O'Hare Intl

Tue 6/24

6:00 am-9:02 am

Nonstop2h 02m

$178

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 6/14

6:00 am-8:41 am

1 stop3h 41m

Chicago Midway

Sat 6/21

5:53 pm-11:00 pm

1 stop4h 07m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

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.

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, 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 $321). 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 April 30, 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 April 30, 2025.

The most flights from USCT to CHI are scheduled on a Tuesday (17 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 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 April 30, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta 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.
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,936 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Spirit Airlines. According to our data, you can fly for as low as $60. Users have also found prices from $69 and $69 on Delta and Southwest, respectively.

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

    The most popular route from Connecticut to Chicago is New York LaGuardia - Chicago O'Hare Intl. You may also consider New York John F Kennedy Intl - 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: SkyWest Airlines (95%), ANA (93%), United Airlines( 90%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $890 for a flight from Connecticut to Chicago. The cheapest flight overall is $136 while the most popular route, (New York LaGuardia - Chicago O'Hare Intl) is currently priced at $117.

  • 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 $321). 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
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.
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
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Newark to Midway flights
John F Kennedy Intl to Midway flights
Los Angeles to O'Hare Intl flights
Boston to O'Hare Intl flights
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San Francisco to O'Hare Intl flights
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San Francisco to Midway flights
Dallas/Fort Worth to Midway flights
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Denver to O'Hare Intl flights
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Raleigh to O'Hare Intl flights
LaGuardia to Midway flights
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Tampa to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
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San Diego to O'Hare Intl flights
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Dulles Intl to Midway flights
Portland to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Hartford to O'Hare Intl flights
Burbank to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Newark to St. Louis flights
Miami to O'Hare Intl flights
Oakland to O'Hare Intl flights
Reagan-National to Midway flights
Baltimore to Midway flights
Boston to Midway flights
Los Angeles to Midway flights
Hobby to Midway flights
Seattle to Midway flights
Minneapolis to O'Hare Intl flights
San Jose to O'Hare Intl flights
Pittsburgh to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Tampa to Midway flights

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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$178FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$207FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$116Average$231FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$125Average$435FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$346FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$218Average$350FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$232Average$385FlexibilityNo cancel feeOn-time63%

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