MDW - BDL

$159 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 7/14. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$337
Typical prices: $597-$542
Delta
Fri 7/31Tue 8/4
MDW - BDL • 1 stop
Cheapest non-stop
$338
Typical prices: $365-$300
Southwest
Sat 9/5Tue 9/8
MDW - BDL • Non-stop
Top airlines
Delta
Cheapest • from $337 (round-trip)
Southwest
Best reviews • 7.9 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 04m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
February
Cheapest • 100% price drop
December
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

Fri, Jul 31 - Tue, Aug 4
Delta Logo
5:10 pm - 11:54 pm
MDW
-
BDL
5h 44m
1 stop
Delta Logo
5:30 am - 9:17 am
BDL
-
MDW
4h 47m
1 stop
$337Delta
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
7:50 am - 11:05 am
MDW
-
BDL
2h 15mnonstop
Southwest Logo
5:55 pm - 7:15 pm
BDL
-
MDW
2h 20mnonstop
$338Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
7:50 am - 11:00 am
MDW
-
BDL
2h 10mnonstop
Southwest Logo
6:30 pm - 8:00 pm
BDL
-
MDW
2h 30mnonstop
$339Southwest
Tue, Jul 7 - Tue, Jul 7
Southwest Logo
5:10 am - 12:15 pm
MDW
-
BDL
6h 05m
1 stop
Southwest Logo
2:35 pm - 10:40 pm
BDL
-
MDW
9h 05m
2 stops
$342Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
5:55 am - 12:20 pm
MDW
-
BDL
5h 25m
1 stop
Southwest Logo
6:20 am - 2:30 pm
BDL
-
MDW
9h 10m
2 stops
$344Southwest
Tue, Jul 21 - Wed, Jul 22
Southwest Logo
11:50 am - 10:50 pm
MDW
-
BDL
10h 00m
2 stops
Southwest Logo
2:35 pm - 10:40 pm
BDL
-
MDW
9h 05m
2 stops
$347Southwest
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
5:55 am - 12:20 pm
MDW
-
BDL
5h 25m
1 stop
Southwest Logo
5:55 pm - 7:15 pm
BDL
-
MDW
2h 20mnonstop
$348Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
5:30 pm - 10:45 pm
MDW
-
BDL
4h 15m
1 stop
Southwest Logo
6:30 pm - 8:00 pm
BDL
-
MDW
2h 30mnonstop
$349Southwest
Thu, Oct 8 - Sat, Oct 10
Southwest Logo
8:55 pm - 8:10 am
MDW
-
BDL
10h 15m
1 stop
Southwest Logo
4:40 pm - 6:00 pm
BDL
-
MDW
2h 20mnonstop
$351Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
11:15 am - 9:10 pm
MDW
-
BDL
8h 55m
1 stop
Southwest Logo
8:00 am - 9:20 am
BDL
-
MDW
2h 20mnonstop
$352Southwest
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 July.

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 Thursday and avoid Tuesdays 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 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$159
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 19% 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 $159 for a one-way ticket and $337 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 $216 or less one-way and $408 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 4235 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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)