MDW - BDL

$79 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 10/21. 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

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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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, Sep 26 - Sun, Sep 28
Frontier Logo
9:48 am - 7:57 pmMDW-BDL
9h 09m1 stop
Frontier Logo
8:37 pm - 7:23 amBDL-MDW
11h 46m1 stop
$176Frontier
Find Deal
Mon, Oct 27 - Thu, Oct 30
Frontier Logo
6:15 am - 3:06 pmMDW-BDL
7h 51m1 stop
Frontier Logo
10:42 am - 10:03 pmBDL-MDW
12h 21m1 stop
$188Frontier
Find Deal
Thu, Nov 6 - Sun, Nov 9
Frontier Logo
10:12 am - 12:41 pmMDW-BDL
25h 29m1 stop
Frontier Logo
10:59 am - 10:03 pmBDL-MDW
12h 04m1 stop
$189Frontier
Find Deal
Tue, Oct 28 - Thu, Oct 30
Delta Logo
6:00 am - 1:17 pmMDW-BDL
6h 17m1 stop
Delta Logo
5:30 am - 8:40 amBDL-MDW
4h 10m1 stop
$197Delta
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
9:48 am - 7:57 pmMDW-BDL
9h 09m1 stop
Frontier Logo
8:37 pm - 7:23 amBDL-MDW
11h 46m1 stop
$201Frontier
Find Deal
Thu, Oct 30 - Thu, Nov 6
Multiple Airlines Logo
9:43 pm - 10:02 amMDW-BDL
35h 19m2 stops
Multiple Airlines Logo
10:42 am - 6:39 pmBDL-MDW
8h 57m1 stop
$204Multiple Airlines
Find Deal
Tue, Nov 4 - Tue, Nov 11
Southwest Logo
6:15 pm - 9:25 pmMDW-BDL
2h 10mnonstop
Southwest Logo
3:40 pm - 9:05 pmBDL-MDW
6h 25m1 stop
$212Southwest
Find Deal
Tue, Nov 4 - Tue, Nov 11
Southwest Logo
6:15 pm - 9:25 pmMDW-BDL
2h 10mnonstop
Southwest Logo
8:55 am - 2:05 pmBDL-MDW
6h 10m2 stops
$217Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Multiple Airlines Logo
8:05 am - 9:09 amMDW-BDL
24h 04m1 stop
Multiple Airlines Logo
8:05 am - 9:47 amBDL-MDW
26h 42m1 stop
$222Multiple Airlines
Find Deal
Tue, Oct 28 - Sat, Nov 1
Delta Logo
5:04 pm - 11:29 pmMDW-BDL
5h 25m1 stop
Delta Logo
5:00 pm - 10:14 pmBDL-MDW
6h 14m1 stop
$255Delta
Find Deal

Everything you should know

Top airlines
Frontier
Cheapest • from $176 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 26% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$176
Typical prices: $275-294
Frontier
Fri 9/26Sun 9/28
MDW - BDL • 1 stop
Cheapest non-stop
$225
Typical prices: $311-435
Southwest
Tue 10/28Sat 11/1
MDW - BDL • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Hartford!
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?

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 Sundays 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 September, where tickets cost $278 (return) on average. On the other hand, the most expensive months are August and May, where the average cost of round-trip tickets is $597 and $483 respectively.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 27% 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 3 days, the lowest price for a flight from Chicago Midway Airport to Hartford was $79 for a one-way ticket and $176 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 $136 or less one-way and $273 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 4242 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

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

Information on your arrival and departure airports

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