$46+ Cheap flights from Chicago (CHI) to Connecticut
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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Feb 27 — Mar 61
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Connecticut 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 Chicago to Connecticut
Cheapest flights from Chicago to ConnecticutExplore the most affordable flight options available from Chicago to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.
Explore the most affordable flight options available from Chicago to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/115:53 pm
ORD
- LGA
Nonstop2h 06m
Spirit Airlines
Wed 2/187:40 am
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$77
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/166:40 am
ORD
- JFK
Nonstop2h 24m
Frontier
Fri 2/2011:03 am
JFK
- ORD
Nonstop3h 00m
Frontier
Deal found 1/28![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:58 pm
ORD
- LGA
Nonstop2h 01m
Spirit Airlines
Fri 2/277:40 am
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$78
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:05 pm
ORD
- JFK
Nonstop2h 24m
Frontier
Mon 3/164:29 pm
JFK
- ORD
Nonstop3h 00m
Frontier
Deal found 1/28![Frontier logo]()
$78
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Tue 2/105:53 pm
ORD
- LGA
Nonstop2h 06m
Spirit Airlines
Wed 2/187:40 am
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 4/236:31 am
ORD
- JFK
Nonstop2h 29m
Frontier
Mon 5/1111:04 am
JFK
- ORD
Nonstop2h 56m
Frontier
Deal found 1/26![Frontier logo]()
$79
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 2/145:58 pm
ORD
- LGA
Nonstop2h 01m
Spirit Airlines
Wed 2/187:40 am
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:31 am
ORD
- JFK
Nonstop2h 29m
Frontier
Sun 4/1911:04 am
JFK
- ORD
Nonstop2h 56m
Frontier
Deal found 1/27![Frontier logo]()
$80
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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.
Wed 3/45:58 pm
ORD
- LGA
Nonstop2h 01m
Spirit Airlines
Sat 3/77:40 am
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 1/26![Spirit Airlines logo]()
$81
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:31 am
ORD
- JFK
Nonstop2h 29m
Frontier
Sun 5/311:04 am
JFK
- ORD
Nonstop2h 56m
Frontier
Deal found 1/27![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:58 pm
ORD
- LGA
Nonstop2h 01m
Spirit Airlines
Fri 2/277:40 am
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Sat 2/145:58 pm
ORD
- LGA
Nonstop2h 01m
Spirit Airlines
Sun 2/227:40 am
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$83
Find flight deals from Chicago to Connecticut
Keep the following information in mind while searching for Chicago to Connecticut flight deals. Data was last updated January 28, 2026.
Round-trip from | $77 (Expedia) |
|---|---|
One-way from | $46 (Trip.com) |
Popular in | November |
Cheapest in | August |
Average price | $327 |
Good round-trip deal | $359 or less |
Good one-way deal | $181 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Connecticut 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 28, 2026.
Use the filters below to find and compare flights from Chicago to Connecticut that are best for you.
Fly from
Chicago
Fly to
Connecticut
Route
Depart
Return
Price
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Fri 2/27
5:58 pm-8:59 pm
Nonstop2h 01m
New York LaGuardia
Mon 3/2
8:45 pm-9:39 am
1 stop13h 54m
$121
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Mon 2/23
8:16 pm-10:57 am
1 stop13h 41m
Newark
Sun 3/1
11:05 pm-12:40 am
Nonstop2h 35m
$121
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Sun 2/15
6:51 pm-10:00 pm
Nonstop2h 09m
Newark
Sun 2/22
11:05 pm-12:40 am
Nonstop2h 35m
$128
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Fri 2/13
6:51 pm-10:00 pm
Nonstop2h 09m
Newark
Mon 2/16
11:05 pm-12:40 am
Nonstop2h 35m
$133
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Thu 3/5
8:55 am-12:12 pm
Nonstop2h 17m
New York LaGuardia
Sun 3/8
7:00 am-8:43 am
Nonstop2h 43m
$137
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 2/24
8:30 am-11:40 am
Nonstop2h 10m
New York LaGuardia
Tue 3/3
6:00 am-7:40 am
Nonstop2h 40m
$137
ChicagoNew York
ORD - JFK
ORDJFK
Chicago O'Hare Intl
Thu 3/5
7:00 am-10:27 am
Nonstop2h 27m
New York John F Kennedy Intl
Mon 3/9
7:50 pm-9:49 pm
Nonstop2h 59m
$137
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Thu 2/26
6:00 am-9:05 am
Nonstop2h 05m
New York LaGuardia
Mon 3/2
6:00 am-7:40 am
Nonstop2h 40m
$137
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Thu 3/5
6:00 am-9:07 am
Nonstop2h 07m
Newark
Sun 3/8
7:30 am-9:21 am
Nonstop2h 51m
$137
ChicagoNew York
ORD - JFK
ORDJFK
Chicago O'Hare Intl
Thu 2/26
7:00 am-10:27 am
Nonstop2h 27m
New York John F Kennedy Intl
Sun 3/1
8:10 am-9:56 am
Nonstop2h 46m
$137
Showing 1-10 of 60 results
Best time to book a flight from Chicago to Connecticut
Have a flexible travel schedule? Discover the best time to fly to Connecticut from Chicago 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 Chicago to Connecticut
What is the cheapest month to book a flight from Chicago to Connecticut?
Currently, September is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $23). Flying from Chicago to Connecticut in February is currently the most expensive (average of $215). 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 CHI to CT?
Find hourly flight availability from Chicago to Connecticut. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 28, 2026.
It’s typically best to fly out from Chicago to Connecticut in the evening. Doing so could potentially save you 31% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Chicago to Connecticut?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Connecticut. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Chicago to Connecticut flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Connecticut
Explore weekly flight availability from Chicago to Connecticut. 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 28, 2026.
The most flights from CHI to USCT 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 (11 on average).
Reviews of airlines servicing Connecticut
Get insights into the airlines that provide service to Connecticut. 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 Connecticut. Reviews last updated January 28, 2026.
Get a feel of what it's like to fly with Southwest, Avelo Airlines, and United Airlines from Chicago to Connecticut by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Avelo Airlines
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Connecticut. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Chicago to Connecticut
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Chicago to Connecticut
Discover the top 4 airlines that operate flights from Chicago to Connecticut. 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 January 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$135 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$362 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$185 | Average$395 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$197 | Average$325 | FlexibilityNo cancel fee | On-time63% |