BDL - MDW

$69 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 8/31. 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.

Flights Deals
Booking Insights
Flights 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 28 - Thu, Sep 4
Southwest Logo
12:40 pm - 2:00 pmBDL-MDW
2h 20mnonstop
Southwest Logo
6:50 pm - 9:55 pmMDW-BDL
2h 05mnonstop
$137Southwest
Find Deal
Thu, Aug 28 - Thu, Sep 4
Southwest Logo
5:30 am - 6:50 amBDL-MDW
2h 20mnonstop
Southwest Logo
2:10 pm - 8:00 pmMDW-BDL
4h 50m1 stop
$147Southwest
Find Deal
Thu, Aug 28 - Tue, Sep 2
Southwest Logo
5:30 am - 6:50 amBDL-MDW
2h 20mnonstop
Southwest Logo
6:10 pm - 9:20 pmMDW-BDL
2h 10mnonstop
$177Southwest
Find Deal
Tue, Aug 19 - Wed, Sep 3
Southwest Logo
5:20 pm - 6:40 pmBDL-MDW
2h 20mnonstop
Southwest Logo
6:10 pm - 9:20 pmMDW-BDL
2h 10mnonstop
$187Southwest
Find Deal
Thu, Aug 21 - Tue, Aug 26
Delta Logo
7:00 am - 11:48 amBDL-MDW
5h 48m1 stop
Delta Logo
1:08 pm - 5:46 pmMDW-BDL
3h 38m1 stop
$197Delta
Find Deal
Thu, Oct 30 - Sat, Nov 1
Frontier Logo
9:54 am - 6:18 pmBDL-MDW
9h 24m1 stop
Frontier Logo
3:59 pm - 1:04 pmMDW-BDL
20h 05m1 stop
$215Frontier
Find Deal
Thu, Sep 25 - Mon, Sep 29
Frontier Logo
10:30 am - 3:58 pmBDL-MDW
6h 28m1 stop
Frontier Logo
8:19 am - 7:57 pmMDW-BDL
10h 38m1 stop
$218Frontier
Find Deal
Thu, Sep 11 - Sun, Sep 14
Frontier Logo
10:30 am - 3:58 pmBDL-MDW
6h 28m1 stop
Frontier Logo
10:13 am - 7:52 pmMDW-BDL
8h 39m1 stop
$219Frontier
Find Deal
Tue, Aug 12 - Tue, Aug 19
Delta Logo
5:35 am - 8:35 amBDL-MDW
4h 00m1 stop
Delta Logo
6:04 am - 1:36 pmMDW-BDL
6h 32m1 stop
$227Delta
Find Deal
Tue, Aug 26 - Thu, Aug 28
Delta Logo
5:35 am - 8:35 amBDL-MDW
4h 00m1 stop
Delta Logo
6:17 pm - 11:21 pmMDW-BDL
4h 04m1 stop
$268Delta
Find Deal
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 September, where tickets cost $319 (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 $416 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 $269, 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 58% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$69
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 15% 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 $69 for a one-way ticket and $137 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.

  • Which is the best airline for flights from Hartford to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Hartford to Chicago are Southwest and Delta. With an average price for the route of $362 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $276 and an overall rating of 8.0.

  • 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 $137 or less one-way and $271 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 airlines 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 4241 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

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

Information on your arrival and departure airports

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