MDW - BDL

$149 Find Cheap Flights from Chicago Midway Airport to Hartford - Compare and Save

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 10/30. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$277
Southwest
Sat 11/7Mon 11/9
MDW - BDL • Non-stop
Cheapest one-way
$149
Typical prices: $213-$596
Southwest
Fri 10/30
MDW - BDL • 1 stop
Top airlines
Cheapest • from $277 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 07m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 100% price drop
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

Sat, Nov 7 - Mon, Nov 9
Southwest Logo
3:40 pm - 6:40 pm
MDW
-
BDL
2h 00mnonstop
Southwest Logo
6:40 pm - 8:05 pm
BDL
-
MDW
2h 25mnonstop
$277Southwest
Tue, Sep 1 - Thu, Sep 3
Southwest Logo
6:25 pm - 9:30 pm
MDW
-
BDL
2h 05mnonstop
Southwest Logo
1:40 pm - 2:55 pm
BDL
-
MDW
2h 15mnonstop
$277Southwest
Sat, Oct 31 - Mon, Nov 2
Southwest Logo
8:35 am - 11:45 am
MDW
-
BDL
2h 10mnonstop
Southwest Logo
6:40 pm - 8:05 pm
BDL
-
MDW
2h 25mnonstop
$277Southwest
Thu, Sep 3 - Thu, Sep 10
Southwest Logo
8:45 am - 12:00 pm
MDW
-
BDL
2h 15mnonstop
Southwest Logo
1:40 pm - 2:55 pm
BDL
-
MDW
2h 15mnonstop
$277Southwest
Tue, Oct 6 - Sat, Oct 10
Southwest Logo
7:45 am - 10:55 am
MDW
-
BDL
2h 10mnonstop
Southwest Logo
4:20 pm - 5:40 pm
BDL
-
MDW
2h 20mnonstop
$277Southwest
Tue, Nov 3 - Sat, Nov 7
Southwest Logo
1:20 pm - 4:20 pm
MDW
-
BDL
2h 00mnonstop
Southwest Logo
3:50 pm - 5:20 pm
BDL
-
MDW
2h 30mnonstop
$277Southwest
Thu, Sep 17 - Tue, Sep 22
Southwest Logo
8:45 am - 12:00 pm
MDW
-
BDL
2h 15mnonstop
Southwest Logo
5:55 pm - 7:15 pm
BDL
-
MDW
2h 20mnonstop
$277Southwest
Tue, Aug 25 - Wed, Aug 26
Southwest Logo
8:45 am - 12:00 pm
MDW
-
BDL
2h 15mnonstop
Southwest Logo
5:55 pm - 7:15 pm
BDL
-
MDW
2h 20mnonstop
$277Southwest
Wed, Aug 26 - Sat, Aug 29
Delta Logo
6:42 pm - 11:51 pm
MDW
-
BDL
4h 09m
1 stop
Delta Logo
1:09 pm - 6:33 pm
BDL
-
MDW
6h 24m
1 stop
$297Delta
Sat, Aug 22 - Wed, Aug 26
Delta Logo
6:42 pm - 11:51 pm
MDW
-
BDL
4h 09m
1 stop
Delta Logo
6:00 am - 11:51 am
BDL
-
MDW
6h 51m
1 stop
$297Delta
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 Saturday 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.

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 July and August, where the average cost of round-trip tickets is $503 and $488 respectively.

Good to know

Low season

October

Cheapest flight

$149
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 10% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Hartford was $149 for a one-way ticket and $277 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 $202 or less one-way and $308 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 4224 reviews
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

it was a short flight, so no refreshments. Could've used some water since I was running from the end of one terminal to the end of another to catch this flight

Easier that prior flight. The airline attendants didn’t really do most of their job as I noted in prior email.

Would like to have screens on back of each seat for entertainment.

The flight attendants were really nice, and of good spirits. Gave all of the safety announcements with a bit of humor and friendly reminders. Easy boarding even as an early c group passenger. Aisle seats available in back of the plane. Coke products and snack mix available. Love the free bag check.

The staff and attendants could have been more helpful with storing carry-ons above in the overhead compartments as well as helping passengers find available seats. There was no food/beverage service due to turbulence There was no internext connectivity due to turbulence The boarding process should be changed entirely and seats should be reserved or assigned to expedite the boarding process.

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

Information on your arrival and departure airports