$54+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Connecticut to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 abril 22, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $115 (Cheapflightsfares) |
One-way from | $54 (Expedia) |
Good round-trip deal | $371 or less |
Good one-way deal | $173 or less |
Find flight deals from Connecticut to Chicago
Cheapest flights from Connecticut to ChicagoExplore 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 abril 22, 2025.
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 abril 22, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 4/22. 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.
This United Airlines deal was found by Cheapflights users on 4/22. 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.
This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 4/22. 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.
This JetBlue deal was found by Cheapflights users on 4/22. 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.
This Delta deal was found by Cheapflights users on 4/22. 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.
This Delta deal was found by Cheapflights users on 4/22. 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.
This CheapOair deal was found by Cheapflights users on 4/22. 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.
This Delta deal was found by Cheapflights users on 4/22. 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.
This Frontier deal was found by Cheapflights users on 4/22. 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.
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 abril 22, 2025.
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
NewarkChicago
EWR - ORD
EWRORD
Newark
dom. 5/18
5:55 am-7:27 am
Nonstop2h 32m
Chicago O'Hare Intl
lun. 5/19
7:35 pm-9:07 am
1 stop12h 32m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
mié. 5/28
6:30 pm-8:07 pm
Nonstop2h 37m
Chicago O'Hare Intl
sáb. 5/31
5:51 am-9:00 am
Nonstop2h 09m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
mié. 5/21
3:30 pm-5:29 pm
Nonstop2h 59m
Chicago O'Hare Intl
mié. 5/28
6:18 pm-10:00 pm
Nonstop2h 42m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
mar. 5/20
6:25 am-8:00 am
Nonstop2h 35m
Chicago O'Hare Intl
mar. 5/27
8:00 pm-11:22 pm
Nonstop2h 22m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
mié. 5/21
6:10 am-7:30 am
Nonstop2h 20m
Chicago Midway
mié. 5/28
8:20 pm-11:25 pm
Nonstop2h 05m
NewarkChicago
EWR - ORD
EWRORD
Newark
mar. 5/20
10:00 pm-9:38 am
1 stop12h 38m
Chicago O'Hare Intl
mar. 5/27
9:08 pm-12:29 am
Nonstop2h 21m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
sáb. 5/24
8:00 pm-9:54 pm
Nonstop2h 54m
Chicago O'Hare Intl
sáb. 5/31
6:10 am-9:28 am
Nonstop2h 18m
NewarkChicago
EWR - MDW
EWRMDW
Newark
mié. 5/28
7:59 am-11:53 am
1 stop4h 54m
Chicago Midway
mar. 6/3
9:16 am-3:59 pm
1 stop5h 43m
NewarkChicago
EWR - ORD
EWRORD
Newark
mié. 5/28
7:07 pm-11:58 pm
1 stop5h 51m
Chicago O'Hare Intl
sáb. 5/31
8:40 am-5:30 pm
1 stop7h 50m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
vie. 5/30
6:30 pm-8:07 pm
Nonstop2h 37m
Chicago O'Hare Intl
dom. 6/1
5:50 am-8:59 pm
1 stop14h 09m
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.
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 abril 22, 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 abril 22, 2025.
The most flights from USCT to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 abril 22, 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.
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Overall
Crew
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
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.
Traveling to a place near Connecticut?
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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.
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 abril 22, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$202 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$207 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$116 | Average$231 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$125 | Average$436 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$350 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$232 | Average$386 | FlexibilityNo cancel fee | On-time63% |