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

Delta, United Airlines, and JetBlue 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 April 2026, 151 flights take off from Hartford and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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

As of April 2026, there are 21 flights per day flying from Hartford to Chicago. The most common time of day flights depart is 6:00AM, with 44% of flights taking off at noon.

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 77% 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.

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 April 2026, 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.

$128 Cheap Flights from Hartford to Chicago in 2026

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 $526 to $362. The lowest price recently found on this route was $337.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Hartford to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:00 am - 8:50 am

BDL

ORD

2h 50mnonstop

8:19 am - 11:45 am

ORD

BDL

2h 26mnonstop

$337American Airlines

Tue, Jun 9 - Sat, Jun 13

7:00 am - 8:25 am

BDL

MDW

2h 25mnonstop

7:40 am - 10:40 am

MDW

BDL

2h 00mnonstop

$338Southwest

Sat, May 23 - Tue, May 26

5:44 pm - 7:51 pm

BDL

ORD

27h 07m

2 stops

8:30 am - 4:30 pm

ORD

BDL

7h 00m

1 stop

$338Multiple Airlines

Mon, May 11 - Wed, May 13

7:43 pm - 7:55 am

BDL

ORD

37h 12m

2 stops

10:27 am - 12:51 am

ORD

BDL

13h 24m

1 stop

$339Multiple Airlines

Sat, May 30 - Sat, Aug 8

3:15 pm - 10:15 pm

BDL

MDW

8h 00m

1 stop

7:40 am - 10:40 am

MDW

BDL

2h 00mnonstop

$340Southwest

Tue, May 12 - Tue, May 19

6:05 am - 11:26 am

BDL

ORD

6h 21m

1 stop

6:08 pm - 9:26 pm

ORD

BDL

2h 18mnonstop

$341United Airlines

Sat, May 16 - Sat, May 16

3:00 pm - 6:15 pm

BDL

MDW

4h 15m

1 stop

7:00 pm - 10:05 pm

MDW

BDL

2h 05mnonstop

$341Southwest

Sat, May 30 - Mon, Jun 1

6:00 am - 11:38 am

BDL

ORD

6h 38m

1 stop

8:00 am - 11:22 am

ORD

BDL

2h 22mnonstop

$343American Airlines

Wed, May 13 - Tue, May 19

11:41 am - 5:56 pm

BDL

MDW

7h 15m

1 stop

6:58 pm - 11:35 pm

MDW

BDL

3h 37m

1 stop

$351Delta

Thu, Jun 4 - Mon, Jun 8

6:00 am - 1:19 pm

BDL

MDW

8h 19m

1 stop

6:23 am - 1:00 pm

MDW

BDL

5h 37m

1 stop

$353Delta

Sat, May 16 - Tue, May 19

American Airlines flights from Hartford to Chicago

Our best American Airlines deals on Hartford to Chicago flight tickets

American Airlines

Jun 9

BDL7:00 amHartford Bradley Intl

2h 50m

ORD8:50 amChicago O'Hare Intl

Jun 13

ORD8:19 amChicago O'Hare Intl

2h 26m

BDL11:45 amHartford Bradley Intl

$337

American Airlines

May 13

BDL2:47 pmHartford Bradley Intl

5h 35m

1 stop

ORD7:22 pmChicago O'Hare Intl

May 16

ORD12:19 pmChicago O'Hare Intl

2h 20m

BDL3:39 pmHartford Bradley Intl

$343

American Airlines

May 16

BDL7:19 pmHartford Bradley Intl

2h 51m

ORD9:10 pmChicago O'Hare Intl

May 18

ORD8:00 amChicago O'Hare Intl

2h 22m

BDL11:22 amHartford Bradley Intl

$346

United Airlines flights from Hartford to Chicago

Our best United Airlines deals on Hartford to Chicago flight tickets

United Airlines

May 16

BDL6:05 amHartford Bradley Intl

6h 21m

1 stop

ORD11:26 amChicago O'Hare Intl

May 16

ORD6:08 pmChicago O'Hare Intl

2h 18m

BDL9:26 pmHartford Bradley Intl

$341

United Airlines

May 11

BDL6:00 amHartford Bradley Intl

2h 48m

ORD7:48 amChicago O'Hare Intl

May 12

ORD7:45 amChicago O'Hare Intl

2h 19m

BDL11:04 amHartford Bradley Intl

$366

United Airlines

May 29

BDL7:45 pmHartford Bradley Intl

4h 41m

1 stop

ORD11:26 pmChicago O'Hare Intl

Jun 1

ORD6:45 amChicago O'Hare Intl

2h 11m

BDL9:56 amHartford Bradley Intl

$367

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 6/9

7:00 am-8:50 am

Nonstop2h 50m

Chicago O'Hare Intl

Sat 6/13

8:19 am-11:45 am

Nonstop2h 26m

$337

Quickest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 5/23

7:00 am-8:25 am

Nonstop2h 25m

Chicago Midway

Tue 5/26

7:40 am-10:40 am

Nonstop2h 00m

$338

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Mon 5/11

5:44 pm-7:51 pm

2 stops27h 07m

Chicago O'Hare Intl

Wed 5/13

8:30 am-4:30 pm

1 stop7h 00m

$338

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 5/30

7:43 pm-7:55 am

2 stops37h 12m

Chicago O'Hare Intl

Sat 8/8

10:27 am-12:51 am

1 stop13h 24m

$339

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 5/12

3:15 pm-10:15 pm

1 stop8h 00m

Chicago Midway

Tue 5/19

7:40 am-10:40 am

Nonstop2h 00m

$340

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 5/16

6:05 am-11:26 am

1 stop6h 21m

Chicago O'Hare Intl

Sat 5/16

6:08 pm-9:26 pm

Nonstop2h 18m

$341

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 5/30

3:00 pm-6:15 pm

1 stop4h 15m

Chicago Midway

Mon 6/1

7:00 pm-10:05 pm

Nonstop2h 05m

$341

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 5/13

6:00 am-11:38 am

1 stop6h 38m

Chicago O'Hare Intl

Tue 5/19

8:00 am-11:22 am

Nonstop2h 22m

$343

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 6/4

11:41 am-5:56 pm

1 stop7h 15m

Chicago Midway

Mon 6/8

6:58 pm-11:35 pm

1 stop3h 37m

$351

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 5/16

6:00 am-1:19 pm

1 stop8h 19m

Chicago Midway

Tue 5/19

6:23 am-1:00 pm

1 stop5h 37m

$353

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 January is, on average, the cheapest month to fly to Chicago from Hartford, with most prices found around $288. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from Hartford to Chicago during October average around $300.

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

Fly from Hartford Bradley Intl to Chicago Midway for the best Hartford Bradley Intl - Chicago flight prices

How far in advance should I book a flight from Hartford 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 $382 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 $281 on momondo.

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

There are 4 cabin classes available to choose from on Hartford 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?

No. A direct flight is the cheapest option for a flight between Hartford to Chicago.

How have Hartford to Chicago flight prices changed over time?

As of April 2026, prices for Hartford to Chicago flights are approximately 28% 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	$215
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Hartford in the past 72 hours is $215. The best round-trip flight deal from Hartford to Chicago found on momondo in the last 72 hours is $428.

The fastest flight from Hartford to Chicago takes 2h 15m

Direct flights go from Hartford to Chicago every day.

There are 3 airports in Chicago. From Hartford there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Hartford to Chicago

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 15m.
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 April 2026, 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 34.87% of the total bookings. Other popular models include Embraer 175 with 16.39%, Embraer 175 (Enhanced Winglets) with 11.58%, and Boeing 737-900 with 10.97%.
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 41% of the total bookings. Other popular airlines include United Airlines with 33%, Southwest with 23%, and JetBlue with 1%.

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
American Airlines	PriceFrom $159	Free Cancellation	Rating 7.1 11,666 reviews	Search American Airlines flights
Delta	PriceFrom $176	Free Cancellation	Rating 7.9 8,450 reviews	Search Delta flights
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,333 reviews	Search Southwest flights
United Airlines	PriceFrom $217	Free Cancellation	Rating 7.4 9,643 reviews	Search United Airlines flights

Southwest Flights From Hartford to Chicago
Southwest flies from Hartford to Chicago around 15 times per week, with 4,332 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 $394 for Southwest flights on this route.
United Airlines Flights From Hartford to Chicago
Across 9,643 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Hartford to Chicago about 24 times each week, with ticket deals ranging from $217 to $402. Price data is based on momondo searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

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

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Sun 5/24

Sun 5/31

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Hartford to Chicago from $128

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 5/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Hartford to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

American Airlines flights from Hartford to Chicago

Our best American Airlines deals on Hartford to Chicago flight tickets

United Airlines flights from Hartford to Chicago

Our best United Airlines deals on Hartford to Chicago flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Hartford to Chicago

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

What is the cheapest month to fly to Chicago?

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

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

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

Can stopping save me money on Hartford to Chicago flights?

How have Hartford to Chicago flight prices changed over time?

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

What airlines fly to Chicago?

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

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

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

Frequently asked questions about flying 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?

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year