BDL - MDW

$90 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 4/23. 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
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$327
Overall average: $440
Southwest
Tue 4/7Wed 4/8
BDL - MDW • Non-stop
Cheapest non-stop
$333
Typical prices: $339-$802
Southwest
Tue 4/14Tue 4/14
BDL - MDW • Non-stop
Top airlines
Cheapest • from $327 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 28m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $156 (round-trip)
Shortest trip • 4h 08m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 51% price drop
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

Tue, Apr 7 - Wed, Apr 8
Southwest Logo
6:20 pm - 7:50 pm
BDL
-
MDW
2h 30mnonstop
Southwest Logo
9:50 am - 3:25 pm
MDW
-
BDL
4h 35m
1 stop
$327Southwest
Fri, Apr 24 - Mon, Apr 27
Frontier Logo
3:34 pm - 10:26 pm
BDL
-
MDW
7h 52m
1 stop
Frontier Logo
6:00 am - 2:49 pm
MDW
-
BDL
7h 49m
1 stop
$330Frontier
Tue, Apr 7 - Tue, Apr 28
Southwest Logo
12:25 pm - 1:50 pm
BDL
-
MDW
2h 25mnonstop
Southwest Logo
9:50 am - 7:00 pm
MDW
-
BDL
8h 10m
2 stops
$332Southwest
Mon, Apr 6 - Sun, Apr 12
Frontier Logo
9:53 pm - 8:07 pm
BDL
-
MDW
23h 14m
2 stops
Frontier Logo
6:00 am - 12:04 pm
MDW
-
BDL
29h 04m
1 stop
$333Frontier
Mon, Apr 6 - Thu, Apr 9
Frontier Logo
12:49 pm - 10:19 pm
BDL
-
MDW
10h 30m
1 stop
Frontier Logo
6:00 am - 1:58 pm
MDW
-
BDL
6h 58m
1 stop
$334Frontier
Thu, Apr 2 - Sat, Apr 4
Frontier Logo
2:55 pm - 8:07 pm
BDL
-
MDW
6h 12m
1 stop
Frontier Logo
6:00 am - 9:01 pm
MDW
-
BDL
14h 01m
1 stop
$335Frontier
Mon, May 11 - Wed, May 13
Southwest Logo
4:40 pm - 10:20 pm
BDL
-
MDW
6h 40m
1 stop
Southwest Logo
12:55 pm - 4:00 pm
MDW
-
BDL
2h 05mnonstop
$336Southwest
Thu, Apr 9 - Fri, Apr 10
Multiple Airlines Logo
7:15 am - 8:07 pm
BDL
-
MDW
13h 52m
2 stops
Multiple Airlines Logo
2:56 pm - 10:05 am
MDW
-
BDL
18h 09m
1 stop
$338Multiple Airlines
Thu, Apr 9 - Sat, Apr 11
Frontier Logo
2:55 pm - 10:21 pm
BDL
-
MDW
8h 26m
1 stop
Frontier Logo
2:56 pm - 1:58 pm
MDW
-
BDL
22h 02m
1 stop
$339Frontier
Wed, May 13 - Sat, May 16
Southwest Logo
6:20 pm - 7:50 pm
BDL
-
MDW
2h 30mnonstop
Southwest Logo
12:45 pm - 10:55 pm
MDW
-
BDL
9h 10m
2 stops
$340Southwest
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, Wednesday 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 Monday 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 March and April, where the average cost of round-trip tickets is $488 and $440 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 $387, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$90
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 13% 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 $90 for a one-way ticket and $327 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.

  • Which airline alliances offer flights from Hartford to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Hartford and Chicago Midway Airport.

  • 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 $389 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 $292 and an overall rating of 7.9.

  • 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 $223 or less one-way and $429 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 4320 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

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

Information on your arrival and departure airports