BDL - MDW

$99 Find Cheap Flights from Hartford to Chicago Midway Airport

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 10/12. 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 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
41,299,237 searches in the past 7 days on KAYAK

Save 22% 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.

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

Sun, Nov 9 - Sat, Nov 15
Frontier Logo
10:59 am - 10:03 pmBDL-MDW
12h 04m1 stop
Frontier Logo
11:36 am - 9:42 amMDW-BDL
21h 06m2 stops
$192Frontier
Find Deal
Sun, Oct 5 - Tue, Oct 7
Delta Logo
5:35 am - 8:40 amBDL-MDW
4h 05m1 stop
Delta Logo
6:23 pm - 11:14 pmMDW-BDL
3h 51m1 stop
$197Delta
Find Deal
Thu, Oct 16 - Tue, Oct 21
Frontier Logo
10:04 am - 11:46 pmBDL-MDW
14h 42m1 stop
Frontier Logo
5:56 pm - 9:09 amMDW-BDL
38h 13m2 stops
$198Frontier
Find Deal
Wed, Oct 29 - Wed, Nov 5
Logo
8:05 am - 9:12 amBDL-MDW
26h 07m1 stop
Logo
2:06 pm - 9:42 amMDW-BDL
18h 36m1 stop
$200
Find Deal
Thu, Oct 2 - Fri, Oct 3
Frontier Logo
10:30 am - 3:58 pmBDL-MDW
6h 28m1 stop
Frontier Logo
9:48 am - 7:57 pmMDW-BDL
9h 09m1 stop
$201Frontier
Find Deal
Sat, Nov 8 - Tue, Nov 11
Frontier Logo
11:13 am - 6:39 pmBDL-MDW
8h 26m1 stop
Frontier Logo
6:26 pm - 9:42 amMDW-BDL
38h 16m2 stops
$202Frontier
Find Deal
Sat, Nov 8 - Tue, Nov 11
Southwest Logo
5:15 pm - 6:45 pmBDL-MDW
2h 30mnonstop
Southwest Logo
9:20 am - 8:05 pmMDW-BDL
9h 45m1 stop
$206Southwest
Find Deal
Sat, Nov 8 - Sat, Nov 15
Frontier Logo
11:13 am - 6:39 pmBDL-MDW
8h 26m1 stop
Frontier Logo
1:37 pm - 9:42 amMDW-BDL
19h 05m1 stop
$208Frontier
Find Deal
Sun, Nov 9 - Tue, Nov 11
Southwest Logo
5:15 am - 6:45 amBDL-MDW
2h 30mnonstop
Southwest Logo
9:20 am - 8:05 pmMDW-BDL
9h 45m1 stop
$218Southwest
Find Deal
Thu, Oct 16 - Tue, Oct 21
Logo
10:04 am - 11:46 pmBDL-MDW
14h 42m1 stop
Logo
8:05 am - 7:06 pmMDW-BDL
10h 01m2 stops
$226
Find Deal

Everything you should know

Top airlines
Frontier
Cheapest • from $192 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 62% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 36% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$192
Overall average: $359
Frontier
Sun 11/9Sat 11/15
BDL - MDW • 1 stop
Cheapest non-stop
$212
Typical prices: $317-532
Southwest
Sun 10/5Tue 10/7
BDL - MDW • Non-stop
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!
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.

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 Tuesday, with Sunday 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 August, where tickets cost $237 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $471 and $414 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 $285, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Hartford to Chicago Midway Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Hartford to Chicago Midway Airport, you should book around 4 weeks before departure, which saves you about 62% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$99
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 7% 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 3 days, the lowest price for a flight from Hartford to Chicago Midway Airport was $99 for a one-way ticket and $192 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, Delta, JetBlue, and Alaska Airlines 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 $170 or less one-way and $314 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.
8.0
SouthwestOverall score based on 4242 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
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 Hartford to Midway

Information on your arrival and departure airports

Hartford (BDL)
Midway (MDW)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.