BDL - MDW

$181 Find Cheap Flights from Hartford to Chicago Midway Airport - 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 Hartford to Midway departing on 6/30. 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

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
Travelers love KAYAK
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Everything you should know

Cheapest round-trip
$356
Typical prices: $294-$184
Southwest
Thu 8/13Sun 8/16
BDL - MDW • Non-stop
Cheapest one-way
$181
Typical prices: $342-$478
Southwest
Tue 6/30
BDL - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $356 (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 25m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $156 (round-trip)
Detroit (DTW)
Shortest trip • 4h 12m (one-way)
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 57% price drop
October
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, Aug 13 - Sun, Aug 16
Southwest Logo
1:40 pm - 2:55 pm
BDL
-
MDW
2h 15mnonstop
Southwest Logo
1:10 pm - 4:15 pm
MDW
-
BDL
2h 05mnonstop
$356Southwest
Thu, Aug 13 - Sun, Aug 16
Southwest Logo
6:20 pm - 7:40 pm
BDL
-
MDW
2h 20mnonstop
Southwest Logo
6:05 am - 2:45 pm
MDW
-
BDL
7h 40m
2 stops
$357Southwest
Wed, Aug 19 - Thu, Aug 27
Delta Logo
7:00 am - 11:51 am
BDL
-
MDW
5h 51m
1 stop
Delta Logo
10:54 am - 6:05 pm
MDW
-
BDL
6h 11m
1 stop
$358Delta
Fri, Jul 3 - Tue, Jul 7
Delta Logo
5:30 am - 9:14 am
BDL
-
MDW
4h 44m
1 stop
Delta Logo
5:10 pm - 11:54 pm
MDW
-
BDL
5h 44m
1 stop
$359Delta
Wed, Jul 29 - Mon, Aug 3
Southwest Logo
6:30 pm - 8:00 pm
BDL
-
MDW
2h 30mnonstop
Southwest Logo
7:45 am - 10:55 am
MDW
-
BDL
2h 10mnonstop
$361Southwest
Sun, Aug 9 - Thu, Aug 20
Delta Logo
5:30 am - 9:17 am
BDL
-
MDW
4h 47m
1 stop
Delta Logo
6:42 pm - 11:51 pm
MDW
-
BDL
4h 09m
1 stop
$362Delta
Tue, Sep 15 - Sat, Sep 19
Southwest Logo
8:10 am - 3:25 pm
BDL
-
MDW
8h 15m
2 stops
Southwest Logo
9:05 am - 3:10 pm
MDW
-
BDL
5h 05m
1 stop
$363Southwest
Sat, Jul 18 - Tue, Jul 21
Southwest Logo
5:15 pm - 10:30 pm
BDL
-
MDW
6h 15m
1 stop
Southwest Logo
7:50 am - 2:00 pm
MDW
-
BDL
5h 10m
2 stops
$364Southwest
Thu, Oct 1 - Sat, Oct 3
Southwest Logo
5:40 pm - 8:45 pm
BDL
-
MDW
4h 05m
1 stop
Southwest Logo
4:15 pm - 7:15 pm
MDW
-
BDL
2h 00mnonstop
$365Southwest
Thu, Aug 13 - Sun, Aug 16
Southwest Logo
5:00 pm - 10:20 pm
BDL
-
MDW
6h 20m
1 stop
Southwest Logo
1:10 pm - 4:15 pm
MDW
-
BDL
2h 05mnonstop
$366Southwest
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.

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

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

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 Thursday, with Tuesday 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 January, where tickets cost $176 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is $832 and $487 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 $433, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$181
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 10% 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 5 days, the lowest price for a flight from Hartford to Chicago Midway Airport was $181 for a one-way ticket and $356 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.

  • 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.

  • 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 $238 or less one-way and $432 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 airline flying 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 4235 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
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 Hartford to Midway

Information on your arrival and departure airports

Hartford (BDL)
Midway (MDW)