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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 37 days early can save you up to 10% on average compared to booking a flight this week. If booking 37 days before your flight isn’t an option for you, users have found flights from Connecticut to Chicago for as little as $177 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 $177 for flights departing within the next 3 days.

Cheap flights from Connecticut to Chicago in September, October 2020

The best prices found for Connecticut to CHI flights for September, October
5 Oct - 13 Oct
$127pp
BDL
Hartford Bradley Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BDL
Hartford Bradley Intl
9 Oct - 13 Oct
$130pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BDL
Hartford Bradley Intl
6 Oct - 13 Oct
$131pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl

Connecticut to Chicago 2020 flight deals

Cheap flights to Chicago from Connecticut found for this year
1 Nov - 5 Nov
$127pp
BDL
Hartford Bradley Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl
9 Oct - 13 Oct
$130pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BDL
Hartford Bradley Intl
6 Oct - 13 Oct
$131pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl

Non-stop flights to Chicago from Connecticut

Save time with Connecticut to Chicago direct flight deals
1 Nov - 5 Nov
$127pp
BDL
Hartford Bradley Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl
6 Oct - 9 Oct
$137pp
BDL
Hartford Bradley Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BDL
Hartford Bradley Intl
19 Oct - 28 Oct
$157pp
BDL
Hartford Bradley Intl
Multiple 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
4 Oct - 9 Oct
$193pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
4 Oct - 7 Oct
$197pp
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
4 Oct - 10 Oct
$209pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BDL
Hartford Bradley Intl

One-way flights to Chicago from Connecticut

The cheapest one-way flights from Connecticut to Chicago
12:20 pm - 6:34 pm
JetBlue
1 Stop
7h 14m
BDL - ORD
JetBlue
5:07 am - 5:27 am
Spirit Airlines
2 Stops
25h 20m
BDL - ORD
Spirit Airlines
$152
KAYAK
12:30 am - 3:55 am
Delta
1 Stop
4h 25m
BDL - MDW
Delta
$320
Delta

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.

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 $127, but on average you can expect to pay $158.

Are there nonstop flights from Connecticut to Chicago for under $200 on Cheapflights?

Cheapflights has at least 15 direct flights from Connecticut to Chicago under $200. A good price for a nonstop flight from Connecticut to Chicago is less than $270.

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, Hartford Bradley Intl - Chicago Midway or Hartford Bradley Intl - Chicago Greater Rockford 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 $117 on average our data indicates $385 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 Qatar Airways (100%), Iberia (100%) or United Airlines (97%) 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 4h 12m. Fly via Delta or Spirit Airlines 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 $138, was found to be the cheapest airline from Connecticut to Chicago. An alternate airline flying to your destination would be Delta.

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

$79 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Spirit Airlines and JetBlue, with prices starting from $114 and $124, 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
Flight duration
2h 24m
Average temperature for September in Chicago
77.0 °F
Avg rainfall for September in Chicago
2.4 ″

Airports servicing

New Haven (HVN)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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