MDW - BDL

$131 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 5/4. 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
$333
Typical prices: $436-$359
Southwest
Wed 5/27Wed 6/3
MDW - BDL • Non-stop
Cheapest one-way
$114
Typical prices: $278-$364
Frontier
Mon 5/4
MDW - BDL • 1 stop
Top airlines
Southwest
Cheapest • from $333 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 02m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
February
Cheapest • 100% price drop
May
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 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

Wed, May 27 - Wed, Jun 3
Southwest Logo
7:40 am - 10:40 am
MDW
-
BDL
2h 00mnonstop
Southwest Logo
6:20 pm - 7:50 pm
BDL
-
MDW
2h 30mnonstop
$333Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
7:40 am - 10:40 am
MDW
-
BDL
2h 00mnonstop
Southwest Logo
6:40 am - 1:45 pm
BDL
-
MDW
8h 05m
1 stop
$343Southwest
Tue, May 26 - Thu, May 28
Southwest Logo
12:55 pm - 4:00 pm
MDW
-
BDL
2h 05mnonstop
Southwest Logo
7:20 pm - 8:45 pm
BDL
-
MDW
2h 25mnonstop
$344Southwest
Tue, Jul 7 - Sat, Jul 11
Southwest Logo
7:50 am - 11:00 am
MDW
-
BDL
2h 10mnonstop
Southwest Logo
5:55 pm - 7:30 pm
BDL
-
MDW
2h 35mnonstop
$347Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
7:40 am - 10:40 am
MDW
-
BDL
2h 00mnonstop
Southwest Logo
11:20 am - 7:25 pm
BDL
-
MDW
9h 05m
2 stops
$348Southwest
Wed, Jun 10 - Tue, Jun 16
Delta Logo
6:58 pm - 11:35 pm
MDW
-
BDL
3h 37m
1 stop
Delta Logo
5:30 am - 9:14 am
BDL
-
MDW
4h 44m
1 stop
$353Delta
Tue, May 26 - Thu, May 28
Southwest Logo
12:55 pm - 4:00 pm
MDW
-
BDL
2h 05mnonstop
Southwest Logo
4:40 pm - 10:20 pm
BDL
-
MDW
6h 40m
1 stop
$354Southwest
Sat, May 23 - Mon, May 25
Southwest Logo
3:45 pm - 6:45 pm
MDW
-
BDL
2h 00mnonstop
Southwest Logo
7:45 am - 9:05 am
BDL
-
MDW
2h 20mnonstop
$355Southwest
Tue, Jul 7 - Sat, Jul 11
Southwest Logo
8:40 am - 3:20 pm
MDW
-
BDL
5h 40m
1 stop
Southwest Logo
5:55 pm - 7:30 pm
BDL
-
MDW
2h 35mnonstop
$357Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
2:35 pm - 10:05 pm
MDW
-
BDL
6h 30m
2 stops
Southwest Logo
11:20 am - 4:15 pm
BDL
-
MDW
5h 55m
1 stop
$358Southwest
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.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Hartford departing in May.

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 Wednesdays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Hartford, 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 Chicago Midway Airport to Hartford is February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are August and April, where the average cost of round-trip tickets is $802 and $474 respectively.

Find deals

Good to know

Low seasonOctober
Cheapest flight$114
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 4% increase in price.
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 $114 for a one-way ticket and $333 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 $474 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.
8.0
SouthwestOverall score based on 4314 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Hartford (BDL)