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Cheap flights from Connecticut (CT) to Chicago (CHI)

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How to find the cheapest flight from
Connecticut to Chicago (CHI)

How far in advance should I book a flight from Connecticut to Chicago?

Users have found that booking a flight from Connecticut to Chicago at least 20 days early can save you up to 10% on average compared to booking a flight this week. If booking 20 days before your flight isn’t an option for you, users have found flights from Connecticut to Chicago for as little as $137 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $157 for flights departing within the next 3 days.

What is the cheapest month to fly from Connecticut to Chicago?

April can be a great time to fly to Chicago from Connecticut with a flight ticket averaging about $135. Cheapflights users have found deals in the month of April for as cheap as $33. The most expensive prices can be found in the month of December.

Cheap flights from Connecticut to Chicago in January, February 2021

The best prices found for Connecticut to CHI flights for January, February
23 Feb - 2 Mar
$126pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BDL
Hartford Bradley Intl
28 Jan - 31 Jan
$128pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
6 Feb - 6 Feb
$133pp
BDL
Hartford Bradley Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
BDL
Hartford Bradley Intl

Connecticut to Chicago 2021 flight deals

Cheap flights to Chicago from Connecticut found for this year
23 Feb - 2 Mar
$126pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BDL
Hartford Bradley Intl
28 Jan - 31 Jan
$128pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
6 Feb - 6 Feb
$133pp
BDL
Hartford Bradley Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
BDL
Hartford Bradley Intl

Non-stop flights to Chicago from Connecticut

Save time with Connecticut to Chicago direct flight deals
6 Feb - 7 Feb
$295pp
BDL
Hartford Bradley Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BDL
Hartford Bradley Intl
5 Feb - 7 Feb
$305pp
BDL
Hartford Bradley Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl
30 Jan - 31 Jan
$315pp
BDL
Hartford Bradley Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BDL
Hartford Bradley Intl

Last minute flights from Connecticut to Chicago

Late deals on round-trip flights to Chicago from Connecticut, departing today and this week
28 Jan - 31 Jan
$128pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
25 Jan - 28 Jan
$134pp
BDL
Hartford Bradley Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BDL
Hartford Bradley Intl
25 Jan - 28 Jan
$158pp
BDL
Hartford Bradley Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl

One-way flights to Chicago from Connecticut

The cheapest one-way flights from Connecticut to Chicago
10:11 am - 6:44 pm
Frontier
1 Stop
9h 33m
BDL - ORD
Frontier
$80
Kiwi.com
1:00 am - 4:00 pm
American Airlines
1 Stop
16h 00m
BDL - ORD
American Airlines
11:55 am - 12:12 pm
Spirit Airlines
3 Stops
25h 17m
BDL - ORD
Spirit Airlines
$117
Gotogate

Related info for your journey

Useful info, stats and facts about Connecticut to Chicago flights.

Flight FAQs

From Connecticut to Chicago

Are flight prices decreasing from Connecticut to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Connecticut and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Connecticut to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travelers safe while flying. New policies for travelers booking flights from Connecticut to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

Which airlines flying from Connecticut to Chicago have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like American Airlines, United Airlines, and Delta flying from Connecticut to Chicago have implemented new flexible cancellation policies.

Can I find flights from Connecticut to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Connecticut to Chicago for under $200. The cheapest flight booked recently is on Multiple Airlines for just $126, but on average you can expect to pay $148.

Are there nonstop flights from Connecticut to Chicago for under $300 on Cheapflights?

Cheapflights has at least 7 direct flights from Connecticut to Chicago under $300. A good price for a nonstop flight from Connecticut to Chicago is less than $383.

Are there last-minute flights available from Connecticut to Chicago for under $200?

There are currently 20+ open flights from Connecticut to Chicago within the next 7 days for less than $200.

What are the most popular airlines that fly from Connecticut to Chicago?

Consider Major Airline, American Airlines or Delta when booking your flight. These represent the most popular airlines when flying from Connecticut to Chicago.

What are the most popular routes from Connecticut to Chicago?

Most travelers choose Hartford Bradley Intl - Chicago O'Hare Intl, New Haven Tweed-New Haven - Chicago O'Hare Intl or Hartford Bradley Intl - Chicago Midway when deciding on the best route from Connecticut to Chicago.

What are the cheapest Flights from Connecticut to Chicago?

Looking at all options, your cheapest flight can be booked for $146. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $128 on average our data indicates $564 when flying from Connecticut to Chicago

What are the most reliable airlines from Connecticut to Chicago?

No one likes to see their flight delayed. When booking a flight from Connecticut to Chicago consider choosing Copa Airlines (100%), SkyWest Airlines (98%) or United Airlines (98%) as they are the most reliable in getting you off to your destination on time.

How long is the flight from Connecticut to Chicago?

There are many flights that can get you from Connecticut to Chicago in 2h 49m. Fly via American Airlines, Delta, or Linear Air Taxi to get the fastest option. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Connecticut to Chicago round-trip?

Spirit Airlines, at $128, was found to be the cheapest airline from Connecticut to Chicago.Alternate airlines to your destination round-trip include American Airlines and Frontier.

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

$55 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and American Airlines, with prices starting from $70 and $103, respectively.

Arrival points for flights from Connecticut to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Connecticut to Chicago
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing

New Haven (HVN)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 airlines flying from Connecticut to Chicago

The chart below displays the airlines Cheapflights users traveling from Connecticut to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$141 $262 No cancel fee 65%
American Airlines
$100 $345 No cancel fee 71%
Delta
$122 $399 No cancel fee N/A
United Airlines
$192 $411 No cancel fee 69%
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