What airlines fly to Chicago?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Hartford according to our data. American Airlines is the first choice among our users, with 83% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Hartford to Chicago on average per day?

As of November 2025, there are 13 flights per day flying from Hartford to Chicago. The most common time of day flights depart is 12:00PM, with 47% of flights taking off in the afternoon.

What is the cheapest airline that flies from Hartford Bradley Intl to Chicago?

Southwest, United Airlines, and Delta are the most popular carriers operating from Hartford Bradley Intl to Chicago

How many flights depart from Hartford to Chicago on average per week?

As of November 2025, 97 flights take off from Hartford and land in Chicago each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.

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?

As of November 2025, there are 4 operators available to choose from 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.

$68 Cheap Flights from Hartford to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Hartford and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $293 to $498. The lowest price recently found on this route was $214.

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:05 am - 9:39 pmBDL-ORD

16h 34m1 stop

5:25 am - 7:06 pmORD-BDL

12h 41m2 stops

$214Multiple Airlines

Find Deal

Fri, Jan 30 - Sun, Feb 1

6:40 am - 2:20 pmBDL-ORD

8h 40m1 stop

3:15 pm - 11:54 pmORD-BDL

7h 39m1 stop

$215JetBlue

Find Deal

Fri, May 1 - Wed, May 6

6:15 am - 8:22 amBDL-ORD

3h 07mnonstop

11:31 am - 7:09 pmORD-BDL

6h 38m1 stop

$217American Airlines

Find Deal

Tue, Dec 16 - Tue, Dec 16

8:05 am - 12:08 pmBDL-ORD

29h 03m2 stops

7:45 am - 4:03 pmORD-BDL

7h 18m1 stop

$222Multiple Airlines

Find Deal

Tue, Jan 13 - Thu, Jan 15

12:16 pm - 2:15 pmBDL-ORD

2h 59mnonstop

1:03 pm - 4:20 pmORD-BDL

2h 17mnonstop

$224American Airlines

Find Deal

Thu, Jan 15 - Sun, Jan 18

5:30 am - 7:05 amBDL-MDW

2h 35mnonstop

1:25 pm - 4:20 pmMDW-BDL

1h 55mnonstop

$225Southwest

Find Deal

Thu, Jan 22 - Tue, Jan 27

5:30 am - 7:05 amBDL-MDW

2h 35mnonstop

9:50 am - 3:55 pmMDW-BDL

5h 05m1 stop

$235Southwest

Find Deal

Tue, Jan 13 - Sat, Jan 17

12:05 pm - 10:12 pmBDL-MDW

11h 07m1 stop

6:15 am - 3:29 pmMDW-BDL

8h 14m1 stop

$238Frontier

Find Deal

Thu, Dec 18 - Mon, Dec 22

6:00 am - 11:55 amBDL-MDW

6h 55m1 stop

6:14 pm - 11:40 pmMDW-BDL

4h 26m1 stop

$245Delta

Find Deal

Wed, Dec 17 - Sun, Jan 18

5:42 pm - 11:47 pmBDL-MDW

7h 05m1 stop

6:40 pm - 11:38 pmMDW-BDL

3h 58m1 stop

$255Delta

Find Deal

Tue, Dec 16 - Wed, Dec 17

JetBlue flights from Hartford to Chicago

Our best JetBlue deals on Hartford to Chicago flight tickets

JetBlue

May 1

BDL6:40 amHartford Bradley Intl

8h 40m

1 stop

ORD2:20 pmChicago O'Hare Intl

May 6

ORD3:15 pmChicago O'Hare Intl

7h 39m

1 stop

BDL11:54 pmHartford Bradley Intl

$215

Find similar

JetBlue

Apr 14

BDL6:45 amHartford Bradley Intl

7h 05m

1 stop

ORD12:50 pmChicago O'Hare Intl

Apr 16

ORD1:45 pmChicago O'Hare Intl

8h 51m

1 stop

BDL11:36 pmHartford Bradley Intl

$236

Find similar

JetBlue

Feb 12

BDL6:00 amHartford Bradley Intl

18h 10m

1 stop

ORD11:10 pmChicago O'Hare Intl

Feb 14

ORD6:04 amChicago O'Hare Intl

16h 53m

1 stop

BDL11:57 pmHartford Bradley Intl

$264

Find similar

American Airlines flights from Hartford to Chicago

Our best American Airlines deals on Hartford to Chicago flight tickets

American Airlines

Dec 16

BDL6:15 amHartford Bradley Intl

3h 07m

ORD8:22 amChicago O'Hare Intl

Dec 16

ORD11:31 amChicago O'Hare Intl

6h 38m

1 stop

BDL7:09 pmHartford Bradley Intl

$217

Find similar

American Airlines

Jan 15

BDL12:16 pmHartford Bradley Intl

2h 59m

ORD2:15 pmChicago O'Hare Intl

Jan 18

ORD1:03 pmChicago O'Hare Intl

2h 17m

BDL4:20 pmHartford Bradley Intl

$224

Find similar

American Airlines

Feb 1

BDL7:00 amHartford Bradley Intl

3h 05m

ORD9:05 amChicago O'Hare Intl

Feb 2

ORD1:03 pmChicago O'Hare Intl

2h 17m

BDL4:20 pmHartford Bradley Intl

$227

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 1/30

6:05 am-9:39 pm

1 stop16h 34m

Chicago O'Hare Intl

Sun 2/1

5:25 am-7:06 pm

2 stops12h 41m

$214

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 5/1

6:40 am-2:20 pm

1 stop8h 40m

Chicago O'Hare Intl

Wed 5/6

3:15 pm-11:54 pm

1 stop7h 39m

$215

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 12/16

6:15 am-8:22 am

Nonstop3h 07m

Chicago O'Hare Intl

Tue 12/16

11:31 am-7:09 pm

1 stop6h 38m

$217

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 1/13

8:05 am-12:08 pm

2 stops29h 03m

Chicago O'Hare Intl

Thu 1/15

7:45 am-4:03 pm

1 stop7h 18m

$222

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 1/15

12:16 pm-2:15 pm

Nonstop2h 59m

Chicago O'Hare Intl

Sun 1/18

1:03 pm-4:20 pm

Nonstop2h 17m

$224

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 1/22

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Tue 1/27

1:25 pm-4:20 pm

Nonstop1h 55m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 1/13

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Sat 1/17

9:50 am-3:55 pm

1 stop5h 05m

$235

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/18

12:05 pm-10:12 pm

1 stop11h 07m

Chicago Midway

Mon 12/22

6:15 am-3:29 pm

1 stop8h 14m

$238

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/17

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Sun 1/18

6:14 pm-11:40 pm

1 stop4h 26m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/16

5:42 pm-11:47 pm

1 stop7h 05m

Chicago Midway

Wed 12/17

6:40 pm-11:38 pm

1 stop3h 58m

$255

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Hartford and Chicago?

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Hartford, with most prices found around $296. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Hartford to Chicago during September average around $301.

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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $366 when searching 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 $282 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.

Can stopping save me money on Hartford to Chicago flights?

You could potentially save up to 7% on your flight if you consider stops on a Hartford to Chicago flight.

How have Hartford to Chicago flight prices changed over time?

As of November 2025, prices for Hartford to Chicago flights are approximately 16% 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	$200
Fastest flight time	2h 25m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Hartford in the past 72 hours is $200. The best round-trip flight deal from Hartford to Chicago found on momondo in the last 72 hours is $362.

The fastest flight from Hartford to Chicago takes 2h 25m

Direct flights go from Hartford to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

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 30m.
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?
As of November 2025, there are 4 operators available to choose from 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?
Based on momondo bookings for flights between Hartford and Chicago, the leading plane model is Boeing 737-800, making up 29.38% of the total bookings. Other popular models include Embraer 175 with 15.84%, Airbus A320-100/200 with 10.65%, and Embraer 175 (Enhanced Winglets) with 8.66%.
What is the most popular airline from Hartford to Chicago?
Based on momondo bookings for flights between Hartford and Chicago, the leading airline is American Airlines, making up 42% of the total bookings. Other popular airlines include United Airlines with 30%, Southwest with 24%, and Frontier with 2%.

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
Frontier	PriceFrom $97	Free Cancellation	Rating 5.8 3,099 reviews	Search Frontier flights
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,254 reviews	Search Southwest flights
American Airlines	PriceFrom $180	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
United Airlines	PriceFrom $218	Free Cancellation	Rating 7.4 9,046 reviews	Search United Airlines flights

Southwest Flights From Hartford to Chicago
Southwest flies from Hartford to Chicago around 10 times per week, with 4,254 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Hartford to Chicago in the last 72 hours was $177 (round-trip), much lower than the average airfare cost of $379 for Southwest flights on this route.
United Airlines Flights From Hartford to Chicago
Across 9,046 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Hartford to Chicago about 17 times each week, with ticket deals ranging from $218 to $432. Price data is based on momondo searches in the last 72 hours.

Merrillville

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

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

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Denverfrom $57

Cheap flights from Hartford to Chicago from $68

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 1/22. 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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JetBlue flights from Hartford to Chicago

Our best JetBlue deals on Hartford to Chicago flight tickets

American Airlines flights from Hartford to Chicago

Our best American Airlines deals on Hartford to Chicago flight tickets

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Use the filters below to find and compare flights from Hartford to Chicago that are best for you.

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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 typical price of a round-trip flight between Hartford and Chicago?

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Hartford, with most prices found around $296. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Hartford to Chicago during September average around $301.

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?

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.

Can stopping save me money on Hartford to Chicago flights?

You could potentially save up to 7% on your flight if you consider stops on a Hartford to Chicago flight.

How have Hartford to Chicago flight prices changed over time?

As of November 2025, prices for Hartford to Chicago flights are approximately 16% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Hartford Bradley Intl to Chicago?

Southwest, United Airlines, and Delta are the most popular carriers operating from Hartford Bradley Intl to Chicago

What airlines fly to Chicago?

How many flights depart from Hartford to Chicago on average per day?

As of November 2025, there are 13 flights per day flying from Hartford to Chicago. The most common time of day flights depart is 12:00PM, with 47% of flights taking off in the afternoon.

How many flights depart from Hartford to Chicago on average per week?

As of November 2025, 97 flights take off from Hartford and land in Chicago each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.

When to book flights from Hartford to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Hartford Bradley Intl to Chicago by plane?

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

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?

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

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

Southwest Flights From Hartford to Chicago

United Airlines Flights From Hartford to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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