MDW - BDL

$81 Find Cheap Flights from Chicago Midway Airport to Hartford

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Hartford departing on 2/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Hartford

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hartford, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hartford, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$175
Multiple Airlines
Fri 1/9Mon 1/12
MDW - BDL • 1 stop
Cheapest non-stop
$285
Southwest
Sat 2/14Mon 2/16
MDW - BDL • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Hartford!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Hartford (MDW-BDL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Hartford that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Hartford

Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
4:31 pm - 11:43 am
MDW
-
BDL
18h 12m1 stop
Multiple Airlines Logo
1:56 pm - 11:09 pm
BDL
-
MDW
10h 13m2 stops
$175Multiple Airlines
Wed, Dec 24 - Wed, Dec 31
Delta Logo
6:08 pm - 11:14 pm
MDW
-
BDL
4h 06m1 stop
Delta Logo
12:48 pm - 5:26 pm
BDL
-
MDW
5h 38m1 stop
$177Delta
Sat, Jan 10 - Sat, Jan 17
Delta Logo
11:45 am - 8:08 pm
MDW
-
BDL
7h 23m1 stop
Delta Logo
2:40 pm - 10:07 pm
BDL
-
MDW
8h 27m1 stop
$245Delta
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
6:40 am - 11:55 am
MDW
-
BDL
4h 15m1 stop
Southwest Logo
9:50 am - 6:40 pm
BDL
-
MDW
9h 50m2 stops
$256Southwest
Wed, Dec 24 - Thu, Jan 1
Southwest Logo
5:35 am - 2:55 pm
MDW
-
BDL
8h 20m1 stop
Southwest Logo
8:55 am - 2:05 pm
BDL
-
MDW
6h 10m2 stops
$259Southwest
Fri, Jan 16 - Sun, Jan 18
Multiple Airlines Logo
8:28 am - 5:48 pm
MDW
-
BDL
8h 20m2 stops
Multiple Airlines Logo
11:46 am - 10:19 pm
BDL
-
MDW
11h 33m1 stop
$269Multiple Airlines
Mon, Jan 12 - Thu, Jan 15
Frontier Logo
4:31 pm - 4:14 pm
MDW
-
BDL
22h 43m2 stops
Frontier Logo
11:46 am - 10:19 pm
BDL
-
MDW
11h 33m1 stop
$273Frontier
Wed, Dec 24 - Wed, Dec 31
Southwest Logo
5:35 am - 2:55 pm
MDW
-
BDL
8h 20m1 stop
Southwest Logo
8:55 am - 2:05 pm
BDL
-
MDW
6h 10m2 stops
$279Southwest
Sat, Feb 14 - Sun, Feb 15
Frontier Logo
8:00 am - 8:15 pm
MDW
-
BDL
11h 15m1 stop
Frontier Logo
2:27 pm - 10:34 pm
BDL
-
MDW
9h 07m1 stop
$281Frontier
Sat, Feb 14 - Sun, Feb 15
Southwest Logo
6:05 pm - 9:05 pm
MDW
-
BDL
2h 00mnonstop
Southwest Logo
6:00 pm - 7:35 pm
BDL
-
MDW
2h 35mnonstop
$285Southwest
Booking Insights

KAYAK's insights & trends for Midway to Hartford flights

Get data-powered insights and trends into flights from Midway to Hartford to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Hartford?

The average price of all round-trip flights from Chicago Midway Airport to Hartford clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Hartford, you should consider leaving on a Tuesday and avoid Mondays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

Good to know

Low seasonMarch
Cheapest flight$81
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from Chicago Midway Airport to Hartford

When to book flights from Midway to Hartford

Are your dates flexible? Find out the best times to travel from Midway to Hartford based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Hartford flights

  • What is the cheapest flight from Chicago Midway Airport to Hartford?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Hartford was $81 for a one-way ticket and $175 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Hartford?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago Midway Airport to Hartford?

    Chicago Midway Airport and Hartford are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Hartford Bradley Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Hartford?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Hartford flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Hartford?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Hartford flight route.

  • On which days can I fly direct from Chicago Midway Airport to Hartford?

    There are nonstop flights from Chicago Midway Airport to Hartford on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Hartford?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Hartford.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Hartford?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hartford from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Hartford?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Hartford with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and BDL can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Hartford?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Hartford from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Hartford

  • Looking for a cheap flight? 25% of our users found flights on this route for $206 or less one-way and $248 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Hartford?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Hartford Bradley Intl.
Find which airlines fly direct from Chicago Midway Airport to Hartford Bradley Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Hartford Bradley Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Hartford Bradley Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to Hartford

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Hartford. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Hartford? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4253 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Everything you need to know for your flight from Midway to Hartford

Information on your arrival and departure airports