BDL - CHI

$139 Find Cheap Flights from Hartford to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$281
Typical prices: $339-$510
JetBlue
Sun 10/14Sun 10/21
BDL - ORD • 1 stop
Cheapest non-stop
$294
Typical prices: $344-$513
Southwest
Fri 11/9Sat 11/17
BDL - MDW • Non-stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and Southwest. Average duration is 2h 44m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 8 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 14% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $159 (round-trip)
Shortest trip • 4h 24m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Hartford to Chicago (BDL-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hartford to Chicago

Wed, Jan 13 - Sat, Jan 16
American Airlines Logo
12:25 pm - 2:30 pmBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
3h 05mnonstop
American Airlines Logo
4:44 pm - 11:41 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
5h 57m1 stop Washington, D.C. Reagan-National
$281American Airlines
Wed, Oct 14 - Wed, Oct 21
JetBlue Logo
6:25 am - 11:24 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
5h 59m1 stop New York John F Kennedy Intl
JetBlue Logo
2:55 pm - 11:58 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
8h 03m1 stop Fort Lauderdale
$281JetBlue
Sat, Dec 5 - Tue, Dec 8
Multiple Airlines Logo
5:31 pm - 1:09 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
8h 38m1 stop Orlando
Multiple Airlines Logo
2:59 pm - 11:59 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
8h 00m1 stop Fort Lauderdale
$281Multiple Airlines
Mon, Oct 5 - Tue, Oct 6
JetBlue Logo
6:25 am - 9:59 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
4h 34m1 stop New York John F Kennedy Intl
JetBlue Logo
3:00 pm - 11:14 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
7h 14m1 stop Fort Lauderdale
$281JetBlue
Fri, Dec 4 - Sun, Dec 6
Frontier Logo
5:31 pm - 1:09 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
8h 38m1 stop Orlando
Frontier Logo
6:15 am - 4:36 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
9h 21m1 stop Orlando
$282Frontier
Wed, Oct 14 - Wed, Oct 21
Southwest Logo
12:55 pm - 4:05 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
4h 10m1 stop Baltimore/Washington
Southwest Logo
7:45 am - 5:45 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
9h 00m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
$284Southwest
Wed, Oct 14 - Wed, Oct 21
Southwest Logo
6:50 am - 2:20 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
8h 30m2 stops Tampa Louisville Intl
Southwest Logo
7:45 am - 5:45 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
9h 00m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
$289Southwest
Thu, Nov 12 - Sat, Nov 14
American Airlines Logo
7:09 am - 9:05 amBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
2h 56mnonstop
American Airlines Logo
8:10 am - 11:25 amORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 15mnonstop
$291American Airlines
Tue, Oct 27 - Sat, Oct 31
United Airlines Logo
12:37 pm - 2:29 pmBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
2h 52mnonstop
United Airlines Logo
6:25 pm - 9:47 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 22mnonstop
$297United Airlines
Thu, Oct 15 - Tue, Oct 27
United Airlines Logo
12:38 pm - 2:23 pmBDL  Hartford Bradley Intl-ORD Chicago O'Hare Intl
2h 45mnonstop
United Airlines Logo
6:25 pm - 9:47 pmORD  Chicago O'Hare Intl-BDL Hartford Bradley Intl
2h 22mnonstop
$297United Airlines
Booking Insights

Price, demand and travel trends for Hartford to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Hartford to Chicago with more confidence.

How much is a round-trip flight from Hartford to Chicago?

Round-trip flights from Hartford to Chicago start at $281. Prices are below average for this route right now, with typical round-trip fares ranging from $339 to $510. The lowest price found in the past 5 days was $281 on JetBlue.

What is the cheapest Hartford to Chicago flight route?

There's little price difference between Hartford to Chicago routes. They average around $409 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Hartford to Chicago?

Saturday is the cheapest day of the week to fly from Hartford to Chicago, it is 6% cheaper than the average day. Monday is the most expensive day with flight prices 13% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • September and October are the cheapest months to fly from Hartford to Chicago at $354 round-trip.
  • June ($475) and July ($470) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 34% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Hartford to Chicago the cheapest?

Flights from Hartford to Chicago are cheapest 8 weeks before departure. Booking in this window typically costs about 43% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Hartford to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Key details for Hartford to Chicago flights

Low season

February

Cheapest flight

$139
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Hartford to Chicago Midway Airport

When to book flights from Hartford to Chicago

Are your dates flexible? Find out the best times to travel from Hartford to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Hartford to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Does BDL International Airport offer services to pets?

    Yes. The airport has three pet relief areas. The areas have two different locations: two at the terminal building and the other at Terminal three. You can carry your pet as you travel. Your pet must remain in his carrier whenever you are in the terminal.

  • Are there services for the disabled at BDL International Airport?

    Yes. Persons with special needs are expected to communicate before their day of travel for the services to be availed. There are wheelchairs that the disabled can be used while at the airport before departing. There are also special lifts for commuter aircraft access.

  • Does Midway International Airport have nursing rooms?

    Yes. The nursing rooms are located in Concourse C near USO Lounge. In these rooms, mothers can easily breastfeed their babies since there is no disruption from other travelers. Mothers can also pump milk for their babies for future use when they have already left the room.

  • Are their family services at O'Hare International Airport?

    Yes. There is a lounge for families located at Terminal 2. It has a space designed for children to play. The amenities available for kids to play with include toys, funhouse mirrors, climbing structures, and airport video games. The children can use all the things available within the airport.

  • Which airlines offer extra legroom and free seat selection on Hartford to Chicago flights?

    Among airlines operating Hartford to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Hartford to Chicago?

    3 airlines operate flights between Hartford and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest

  • Which airports can I use when flying from Hartford to Chicago?

    Flights from Hartford to Chicago usually depart from Hartford Bradley Intl (BDL) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airlines include bags at no extra cost on Hartford to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Hartford to Chicago?

    Three cabin classes are available on flights from Hartford to Chicago:

    • Economy Class
    • Business Class
    • First Class

  • How much can I save by taking a layover when flying from Hartford to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $159 round-trip via Orlando (MCO), compared to $412 for nonstop.

  • What is the standard checked-bag allowance on flights from Hartford to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Hartford to Chicago pass through?

    One-stop flights from Hartford to Chicago most commonly connect through:

    • New York John F Kennedy Intl (JFK) - 43% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 31% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 7% of one-stop connections
    • Orlando (MCO) - 7% of one-stop connections

    New York John F Kennedy Intl (JFK) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Hartford to Chicago?

    On the Hartford to Chicago route, being flexible with your departure day can save you up to 17%. Saturday is the cheapest day at $386 round-trip on average, while Monday is the most expensive at $465: a $79 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • How are flight departures from Hartford to Chicago spread across the day?

    Morning is the busiest departure period on Hartford to Chicago flights, with 40% of flights leaving in that window. Afternoon departures account for 30%, evening flights for 30%, and night flights for 0%.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • What are the earliest and latest flights from Hartford to Chicago?

    These are the earliest and latest flight times available from Hartford to Chicago:

    • Earliest: departs at 6:00 am and lands at 8:44 am
    • Latest: departs at 8:40 pm and lands at 11:24 pm.

    The flight takes about 2h 44m.

  • How expensive are last-minute Hartford to Chicago flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 59% above the route average of $409. Book 8 weeks before departure for the lowest fares.

  • How long is a flight from Hartford to Chicago?

    A nonstop flight from Hartford to Chicago takes 2h 44m, covering 767 miles.

  • Do I need a passport to fly from Hartford to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Hartford to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $281 to $2,088. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Hartford to Chicago looking right now?

    One-way fares from Hartford to Chicago are currently lower than usual. Average one-way flight prices are about $144, which is 42% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Hartford to Chicago?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 24m, compared with 5h 19m via Baltimore/Washington (BWI) and 6h 08m via Chicago O'Hare Intl (ORD).

  • What is the time difference between Hartford and Chicago?

    Chicago is 1 hour behind Hartford (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Dollar
    • Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • How much should I expect to pay for a Hartford to Chicago flight?

    Round-trip flights from Hartford to Chicago range from $339 to $510, with an average of $409 over the past 12 months. Anything below $339 counts as a good deal.

  • Which airlines offer Wi-Fi on Hartford to Chicago flights?

    American Airlines is the only airline on the Hartford to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Hartford to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Saturday departure instead of Monday. On this route, Saturday flights average $386 - about $79 less than Monday (17% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 8 weeks before you fly. On this route, that window historically saves about 43% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Hartford to Chicago trip for September. Fares historically average $354 round-trip in that month - typically $121 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Orlando Airport (MCO) can be cheaper than flying direct. The cheapest layover option averages $159 round-trip on this route - about $253 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel
  • Hartford Bradley International Airport (BDL) offers parking facilities to travelers. There is no specific procedure needed for parking. No reservation is also needed for one to park. You are allowed to park on arrival. The parking locations include Express Lot 1, Economy Lot 2, and economy lot 4. All the parking lots have varying rates, depending on the duration you are to park at the airport.
  • BDL International Airport has lounges where you can have some rest before you depart from the airport. Escape Lounges is accessible by all the travelers departing from the airport to enjoy the facilities. It offers complimentary access to American Express Platinum and Delta SkyMiles. To access the lounge, you only need a member's card.
  • BDL International Airport has a mothers' nursing lounge where they can freely feed their babies without interference. It is easier and more comfortable for the mother to take care of their children in the nursing room. It is located next to the CNBC store. It also has a changing table where the mother can change diapers for the baby. The airport also has a power outlet for the mothers who use electric pumps.
  • O'Hare International airport (ORD) in Chicago has a business center for travelers who are on a business vacation. There are meeting rooms where you can meet with your partners and discuss. It also offers fax, copying, packaging, and shipping services. A business traveler can connect to other partners online because the place has free internet access.
  • Midway International Airport (MDW) in Chicago has car rental facilities that they offer travelers on arrival. A traveler is allowed to rent a car to use for a given period once they have arrived at the airport. The service is offered at fair prices that every traveler in need can access.

Prefer to fly direct from Hartford to Chicago?

 
Find which airlines fly direct from Hartford Bradley Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Hartford Bradley Intl to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Hartford Bradley Intl

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

More options for your flight from Hartford to Chicago

Complete your trip to Chicago with a hotel stay or car rental