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Cheap flights from Hartford to Chicago from $55

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hartford to Chicago departing on 2/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Hartford to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Hartford to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Hartford to Chicago.

Cheap last minute flights

Planning a quick getaway from Hartford to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Hartford to Chicago

Find recent round-trip train or bus tickets from Hartford to Chicago.

All round-trip flight deals from Hartford to Chicago

The cheapest plane tickets from Hartford to Chicago found on KAYAK recently.
2:28 pm - 11:58 pmBDL-MDW
10h 30m1 stop
8:30 am - 11:07 amMDW-BDL
25h 37m1 stop
$120Frontier
Find Deal
Mon, Feb 24 - Tue, Feb 25
2:59 pm - 11:58 pmBDL-MDW
9h 59m1 stop
7:25 am - 6:42 pmMDW-BDL
10h 17m1 stop
$130Frontier
Find Deal
Mon, Mar 10 - Thu, Mar 13
11:17 am - 10:40 amBDL-ORD
24h 23m1 stop
2:29 pm - 10:41 amORD-BDL
19h 12m1 stop
$147Spirit Airlines
Find Deal
Mon, Mar 3 - Tue, Mar 4
11:17 am - 10:03 pmBDL-ORD
11h 46m1 stop
5:00 am - 10:22 amORD-BDL
28h 22m1 stop
$161Spirit Airlines
Find Deal
Fri, Feb 21 - Mon, Feb 24
6:05 am - 8:00 amBDL-ORD
2h 55mnonstop
6:15 pm - 9:27 pmORD-BDL
2h 12mnonstop
$257United Airlines
Find Deal
Tue, Feb 18 - Tue, Feb 25
7:00 am - 8:35 amBDL-MDW
2h 35mnonstop
11:30 am - 2:30 pmMDW-BDL
2h 00mnonstop
$257Southwest
Find Deal
Thu, Feb 13 - Mon, Feb 17
12:15 pm - 2:16 pmBDL-ORD
3h 01mnonstop
6:14 pm - 11:59 pmORD-BDL
4h 45m1 stop
$263United Airlines
Find Deal
Thu, Feb 20 - Thu, Feb 27
12:25 pm - 2:19 pmBDL-ORD
2h 54mnonstop
1:43 pm - 6:24 pmORD-BDL
3h 41m1 stop
$267American Airlines
Find Deal
Thu, Feb 13 - Tue, Feb 18
7:55 am - 12:25 pmBDL-MDW
5h 30m1 stop
7:40 pm - 10:50 pmMDW-BDL
2h 10mnonstop
$267Southwest
Find Deal
Tue, May 6 - Tue, May 13
5:10 am - 10:38 amBDL-ORD
6h 28m1 stop
8:34 am - 11:45 amORD-BDL
2h 11mnonstop
$268American Airlines
Find Deal
Mon, Mar 10 - Thu, Mar 13
11:40 am - 6:20 pmBDL-MDW
7h 40m1 stop
$55Frontier
Find Deal
Thu, Feb 27
2:28 pm - 11:58 pmBDL-MDW
10h 30m1 stop
$61Frontier
Find Deal
Mon, Feb 24
11:17 am - 10:03 pmBDL-ORD
11h 46m1 stop
$74Spirit Airlines
Find Deal
Tue, Mar 4
11:17 am - 10:03 pmBDL-ORD
11h 46m1 stop
$78Spirit Airlines
Find Deal
Wed, Feb 26
1:02 pm - 2:45 pmBDL-ORD
2h 43mnonstop
$129United Airlines
Find Deal
Tue, May 6
7:30 am - 9:15 amBDL-MDW
2h 45mnonstop
$129Southwest
Find Deal
Mon, Feb 24
7:00 am - 8:51 amBDL-ORD
2h 51mnonstop
$130American Airlines
Find Deal
Mon, Feb 24
12:20 pm - 6:35 pmBDL-MDW
7h 15m1 stop
$138Southwest
Find Deal
Tue, Feb 25
6:32 am - 8:15 amBDL-ORD
2h 43mnonstop
$149American Airlines
Find Deal
Fri, Mar 14
6:05 am - 8:00 amBDL-ORD
2h 55mnonstop
$164United Airlines
Find Deal
Wed, Feb 19
10:45 am - 11:33 pmBDL-ORD
13h 48m1 stop
10:33 am - 8:18 amORD-BDL
20h 45m1 stop
$299Frontier
Find Deal
Sun, Jan 26 - Thu, Jan 30
7:40 pm - 10:16 pmBDL-ORD
27h 36m1 stop
3:56 pm - 5:05 pmORD-BDL
24h 09m1 stop
Sun, Jan 26 - Wed, Jan 29
6:00 pm - 11:32 pmBDL-ORD
30h 32m1 stop
3:56 pm - 5:05 pmORD-BDL
24h 09m1 stop
$328Spirit Airlines
Find Deal
Mon, Jan 27 - Wed, Jan 29
6:00 pm - 8:13 pmBDL-ORD
27h 13m1 stop
3:56 pm - 5:05 pmORD-BDL
24h 09m1 stop
$353Spirit Airlines
Find Deal
Mon, Jan 27 - Wed, Jan 29
10:40 am - 8:07 amBDL-ORD
22h 27m2 stops
10:55 am - 2:07 pmORD-BDL
2h 12mnonstop
$419United Airlines
Find Deal
Sat, Jan 25 - Sun, Jan 26
7:56 pm - 2:34 pmBDL-ORD
19h 38m1 stop
6:25 pm - 9:43 pmORD-BDL
2h 18mnonstop
$429United Airlines
Find Deal
Sat, Jan 25 - Sun, Jan 26
6:00 am - 7:45 amBDL-MDW
2h 45mnonstop
12:25 pm - 3:25 pmMDW-BDL
2h 00mnonstop
$801Southwest
Find Deal
Mon, Jan 27 - Tue, Jan 28
6:30 am - 11:45 amBDL-MDW
6h 15m1 stop
12:25 pm - 3:25 pmMDW-BDL
2h 00mnonstop
$811Southwest
Find Deal
Mon, Jan 27 - Tue, Jan 28
7:05 am - 8:54 amBDL-ORD
2h 49mnonstop
6:30 pm - 9:42 pmORD-BDL
2h 12mnonstop
$900American Airlines
Find Deal
Sun, Jan 26 - Tue, Jan 28
5:55 pm - 7:44 pmBDL-ORD
2h 49mnonstop
4:02 pm - 11:44 pmORD-BDL
6h 42m1 stop
$910American Airlines
Find Deal
Sun, Jan 26 - Tue, Jan 28
7:00 am - 8:35 amBDL-MDW
2h 35mnonstop
8:20 pm - 11:25 pmMDW-BDL
2h 05mnonstop
$257Southwest
Find Deal
Thu, Feb 13 - Mon, Feb 17
6:05 am - 8:00 amBDL-ORD
2h 55mnonstop
6:15 pm - 9:27 pmORD-BDL
2h 12mnonstop
$257United Airlines
Find Deal
Tue, Feb 18 - Tue, Feb 25
6:32 am - 8:15 amBDL-ORD
2h 43mnonstop
8:34 am - 11:45 amORD-BDL
2h 11mnonstop
$259American Airlines
Find Deal
Mon, Mar 10 - Thu, Mar 13
4:57 pm - 6:50 pmBDL-ORD
2h 53mnonstop
10:55 am - 2:06 pmORD-BDL
2h 11mnonstop
$277United Airlines
Find Deal
Wed, Mar 5 - Fri, Mar 7
6:05 pm - 7:30 pmBDL-MDW
2h 25mnonstop
6:35 pm - 9:40 pmMDW-BDL
2h 05mnonstop
$277Southwest
Find Deal
Tue, Apr 8 - Fri, Apr 11
4:57 pm - 6:50 pmBDL-ORD
2h 53mnonstop
10:54 am - 2:05 pmORD-BDL
2h 11mnonstop
$290United Airlines
Find Deal
Sat, Feb 22 - Mon, Feb 24
8:00 pm - 9:35 pmBDL-MDW
2h 35mnonstop
11:30 am - 2:30 pmMDW-BDL
2h 00mnonstop
$297Southwest
Find Deal
Fri, Feb 21 - Fri, Feb 28
12:21 pm - 2:15 pmBDL-ORD
2h 54mnonstop
7:05 pm - 10:14 pmORD-BDL
2h 09mnonstop
$298American Airlines
Find Deal
Sat, Mar 8 - Sat, Mar 15
7:00 am - 8:51 amBDL-ORD
2h 51mnonstop
7:36 pm - 10:36 pmORD-BDL
2h 00mnonstop
$345American Airlines
Find Deal
Fri, Feb 21 - Sun, Feb 23
5:51 pm - 7:45 pmBDL-ORD
2h 54mnonstop
8:30 am - 11:44 amORD-BDL
2h 14mnonstop
$358American Airlines
Find Deal
Tue, Feb 18 - Fri, Feb 21

Frontier flights from Hartford to Chicago

Our best Frontier deals on Hartford to Chicago flight tickets
Frontier
Feb 24
BDL2:28 pmHartford Bradley Intl
10h 30m
1 stop
MDW11:58 pmChicago Midway
Feb 25
MDW8:30 amChicago Midway
25h 37m
1 stop
BDL11:07 amHartford Bradley Intl
Frontier
Feb 7
BDL1:17 pmHartford Bradley Intl
11h 16m
1 stop
ORD11:33 pmChicago O'Hare Intl
Feb 9
ORD7:00 amChicago O'Hare Intl
10h 40m
1 stop
BDL6:40 pmHartford Bradley Intl
Frontier
Mar 10
BDL4:24 pmHartford Bradley Intl
8h 34m
1 stop
MDW11:58 pmChicago Midway
Mar 13
MDW7:25 amChicago Midway
10h 17m
1 stop
BDL6:42 pmHartford Bradley Intl

Spirit Airlines flights from Hartford to Chicago

Our best Spirit Airlines deals on Hartford to Chicago flight tickets
Spirit Airlines
Mar 3
BDL11:17 amHartford Bradley Intl
24h 23m
1 stop
ORD10:40 amChicago O'Hare Intl
Mar 4
ORD2:29 pmChicago O'Hare Intl
19h 12m
1 stop
BDL10:41 amHartford Bradley Intl
Spirit Airlines
Feb 21
BDL11:17 amHartford Bradley Intl
11h 46m
1 stop
ORD10:03 pmChicago O'Hare Intl
Feb 24
ORD5:00 amChicago O'Hare Intl
28h 22m
1 stop
BDL10:22 amHartford Bradley Intl
Spirit Airlines
Mar 6
BDL11:36 amHartford Bradley Intl
13h 31m
1 stop
ORD12:07 amChicago O'Hare Intl
Mar 11
ORD7:42 pmChicago O'Hare Intl
13h 59m
1 stop
BDL10:41 amHartford Bradley Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Hartford to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Hartford, with most prices found around $315. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Hartford to Chicago during August average around $318.

What is the cheapest Hartford Bradley Intl to Chicago flight route?

Fly from Hartford Bradley Intl to Chicago O'Hare Intl for the best Hartford Bradley Intl - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Hartford when booking 10 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $368 when searching 10 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Hartford for as low as $312 on momondo.

What cabin class options are available on Hartford Bradley Intl to Chicago flights?

There are 4 cabin classes available to choose from on Hartford Bradley Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Hartford to Chicago flight prices changed over time?

As of January 2025, prices for Hartford to Chicago flights are approximately 146% more expensive when compared to flights at the same time last year.

When to book flights from Hartford to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Hartford to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Hartford to Chicago (BDL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hartford to Chicago

Best Price Found

$55

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Hartford in the past 72 hours is $55. The best round-trip flight deal from Hartford to Chicago found on momondo in the last 72 hours is $120.
The fastest flight from Hartford to Chicago takes 2h 20m
Direct flights go from Hartford to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Hartford Bradley Intl to Chicago by plane?

    Chicago is 768.4 mi away from Hartford Bradley Intl. A reasonable flight in good conditions will take 2h 20m.

  • When did momondo last update prices for flights from Hartford Bradley Intl Airport to Chicago?

    Prices for flights from Hartford Bradley Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Hartford Bradley Intl Airport to Chicago?

  • How old do you have to be to fly from Hartford Bradley Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Hartford Bradley Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Hartford to Chicago?

  • What is the most popular airline from Hartford to Chicago?


Best airlines flying from Hartford to Chicago

Compare and see reviews for airlines that fly from Hartford to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $108Free CancellationRating
6.0
3,441 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $117Free CancellationRating
6.3
8,111 reviews
Search Spirit Airlines flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,512 reviews
Search Delta flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
8,975 reviews
Search United Airlines flights
SouthwestPriceFrom $232Free CancellationRating
8.1
4,654 reviews
Search Southwest flights
  • Southwest Flights From Hartford to Chicago

    Southwest flies from Hartford to Chicago around 9 times per week, with 4,654 momondo users rating the airline 8.1/10. The cheapest Southwest deal from Hartford to Chicago in the last 72 hours was $232 (round-trip), much lower than the average airfare cost of $368 for Southwest flights on this route.

  • United Airlines Flights From Hartford to Chicago

    Across 8,975 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Hartford to Chicago about 12 times each week, with ticket deals ranging from $218 to $400. Price data is based on momondo searches in the last 72 hours.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Hartford to Chicago?

Finding the right flight to Chicago from Hartford is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Hartford to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Hartford which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Hartford to Chicago?

Once you have performed a search for Hartford to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Hartford to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Hartford to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


An easier way to manage your Chicago trip

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago