BDL - MDW

$70 Find Cheap Flights from Hartford to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hartford to Midway departing on 2/7. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hartford to Chicago, 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 Hartford to Chicago, as well as popular online travel agencies
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$197
Overall average: $377
Frontier
Thu 2/26Sun 3/1
BDL - MDW • 1 stop
Cheapest non-stop
$225
Typical prices: $329-$562
Southwest
Wed 1/14Sun 1/18
BDL - MDW • Non-stop
Top airlines
Delta
Cheapest • from $177 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
August
Cheapest • 35% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hartford to Midway (BDL-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hartford to Midway 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 Hartford to Midway

Thu, Feb 26 - Sun, Mar 1
Frontier Logo
2:27 pm - 10:29 pm
BDL
-
MDW
9h 02m1 stop
Frontier Logo
7:30 am - 10:07 am
MDW
-
BDL
25h 37m1 stop
$197Frontier
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
10:52 am - 8:32 pm
BDL
-
MDW
10h 40m1 stop
Frontier Logo
7:30 am - 5:05 pm
MDW
-
BDL
8h 35m1 stop
$213Frontier
Wed, Jan 14 - Sun, Jan 18
Southwest Logo
5:30 am - 7:05 am
BDL
-
MDW
2h 35mnonstop
Southwest Logo
1:25 pm - 4:20 pm
MDW
-
BDL
1h 55mnonstop
$225Southwest
Thu, Jan 22 - Sat, Jan 24
Frontier Logo
12:11 pm - 10:19 pm
BDL
-
MDW
11h 08m1 stop
Frontier Logo
9:38 am - 11:16 am
MDW
-
BDL
24h 38m1 stop
$230Frontier
Fri, Feb 27 - Sun, Mar 1
Frontier Logo
10:33 am - 2:55 pm
BDL
-
MDW
29h 22m1 stop
Frontier Logo
7:30 am - 10:07 am
MDW
-
BDL
25h 37m1 stop
$232Frontier
Wed, Jan 14 - Sun, Jan 18
Southwest Logo
12:15 pm - 9:00 pm
BDL
-
MDW
9h 45m1 stop
Southwest Logo
1:25 pm - 4:20 pm
MDW
-
BDL
1h 55mnonstop
$235Southwest
Wed, Jan 14 - Sun, Jan 18
Southwest Logo
6:00 am - 1:55 pm
BDL
-
MDW
8h 55m2 stops
Southwest Logo
1:25 pm - 4:20 pm
MDW
-
BDL
1h 55mnonstop
$240Southwest
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
10:52 am - 8:32 pm
BDL
-
MDW
10h 40m1 stop
Frontier Logo
7:30 am - 5:05 pm
MDW
-
BDL
8h 35m1 stop
$242Frontier
Wed, Jan 14 - Sat, Jan 17
Delta Logo
12:56 pm - 5:34 pm
BDL
-
MDW
5h 38m1 stop
Delta Logo
6:45 am - 1:33 pm
MDW
-
BDL
5h 48m1 stop
$245Delta
Wed, Jan 14 - Wed, Jan 21
Multiple Airlines Logo
8:05 am - 10:32 am
BDL
-
MDW
27h 27m1 stop
Multiple Airlines Logo
1:20 pm - 11:16 am
MDW
-
BDL
20h 56m1 stop
$258Multiple Airlines
Booking Insights

KAYAK's insights & trends for Hartford to Midway flights

Get data-powered insights and trends into flights from Hartford to Midway 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 Hartford to Chicago Midway Airport?

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

For Hartford to Chicago Midway Airport, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to Hartford, the best deals are generally found on Tuesday, with Monday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Hartford to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Hartford to Chicago Midway Airport is August, where tickets cost $237 (return) on average. On the other hand, the most expensive months are March and July, where the average cost of round-trip tickets is $471 and $405 respectively.

Can I save money by flying with a layover from Hartford to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $322, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$70
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Hartford to Chicago Midway Airport

When to book flights from Hartford to Midway

Are your dates flexible? Find out the best times to travel from Hartford to Midway 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 Hartford to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Hartford to Chicago Midway Airport was $70 for a one-way ticket and $197 for a round-trip.

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

    A passport is not required to fly from Hartford to Chicago Midway Airport.

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

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Hartford to Chicago Midway Airport flight route.

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

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

  • Which airline alliances offer flights from Hartford to Chicago Midway Airport?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Hartford and Chicago Midway Airport, with SkyTeam being the most commonly used for this route.

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

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

  • Which is the best airline for flights from Hartford to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Hartford to Chicago are Southwest and Delta. With an average price for the route of $374 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $287 and an overall rating of 7.9.

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

    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 Hartford to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Hartford 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 Hartford to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Hartford with another airline. Booking your flights between Hartford and MDW 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 Hartford to Chicago Midway Airport?

    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 Chicago Midway Airport from Hartford 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 Hartford to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $223 or less one-way and $402 or less round-trip.

Prefer to fly direct from Hartford to Chicago Midway Airport?

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

Direct departures

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

Direct returns

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

Reviews of the top 3 airlines serving from Hartford to Midway

 
See real verified KAYAK customer reviews for airlines flying from Hartford to Chicago. 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 Hartford to Midway? 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 4250 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

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.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

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

Information on your arrival and departure airports