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BDL - MDW

Find cheap flights from Hartford to Chicago Midway Airport from $59

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 5/19. 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
0 bags
Wed 6/5
Wed 6/12

Search 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
In the last 7 days travelers have searched 42,830,901 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
7:59 pm - 9:55 pmBDL-MDW
26h 56m1 stop
12:15 pm - 8:35 pmMDW-BDL
7h 20m1 stop
$152Frontier
Find Deal
Thu, Aug 15 - Fri, Aug 23
9:07 pm - 6:54 amBDL-MDW
10h 47m1 stop
9:12 pm - 8:55 amMDW-BDL
10h 43m1 stop
$153Frontier
Find Deal
Tue, May 28 - Thu, May 30
8:51 pm - 9:31 amBDL-MDW
13h 40m1 stop
5:14 pm - 3:17 pmMDW-BDL
21h 03m1 stop
$156Frontier
Find Deal
Sat, Jun 8 - Mon, Jun 10
7:54 pm - 6:54 amBDL-MDW
12h 00m2 stops
9:53 pm - 9:10 amMDW-BDL
10h 17m1 stop
$158Frontier
Find Deal
Sat, Jun 1 - Sun, Jun 2
7:38 pm - 6:48 pmBDL-MDW
24h 10m1 stop
10:08 am - 7:09 pmMDW-BDL
8h 01m1 stop
$160Frontier
Find Deal
Thu, Sep 12 - Sat, Sep 14
6:46 pm - 12:46 amBDL-MDW
7h 00m1 stop
8:51 pm - 6:45 pmMDW-BDL
20h 54m1 stop
$168Frontier
Find Deal
Thu, May 30 - Thu, Jun 6
6:46 pm - 12:46 amBDL-MDW
7h 00m1 stop
9:53 pm - 9:10 amMDW-BDL
10h 17m1 stop
$169Frontier
Find Deal
Thu, May 30 - Sun, Jun 2
9:15 am - 2:41 pmBDL-MDW
6h 26m1 stop
7:49 am - 7:06 pmMDW-BDL
10h 17m1 stop
$170Frontier
Find Deal
Wed, May 29 - Thu, May 30
5:45 am - 8:48 amBDL-MDW
4h 03m1 stop
5:45 pm - 11:28 pmMDW-BDL
4h 43m1 stop
$276Delta
Find Deal
Wed, Jun 19 - Tue, Jun 25
9:35 am - 12:31 pmBDL-MDW
3h 56m1 stop
5:59 pm - 11:35 pmMDW-BDL
4h 36m1 stop
$291Delta
Find Deal
Tue, Aug 13 - Sat, Aug 17

Flights from Hartford to Midway - Travel Insights & Trends

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 flights from Hartford to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Monday and more expensive on a Wednesday. On your return trip to Hartford, you should consider flying back on a Tuesday, and avoid Mondays for better deals.

Which airlines provide the cheapest flights from Hartford to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($59) and Delta ($138). The cheapest round-trip tickets were found on Frontier ($152) and Delta ($276).

How many flights are there between Hartford and Chicago Midway Airport per day?

Each day, there are between 1 and 5 nonstop flights that take off from Hartford and land in Chicago Midway Airport, with an average flight time of 2h 22m. The most common departure time is 7:00 pm and most flights take off in the morning. Each week, there are 28 flights. The most frequent day of departure is Friday, when 18% of all weekly flights depart. The fewest flights depart on a Saturday.

What’s the earliest departure time from Hartford to Chicago Midway Airport?

Early birds can take the earliest flight from Hartford at 5:30 am and will be landing in Chicago Midway Airport at 6:50 am.

What’s the latest departure time from Hartford to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Hartford to Chicago Midway Airport jets off at 8:25 pm and lands at 9:50 pm.

Good to know

Low season

January

High season

April

Cheapest flight

$59
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 33% 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 $59 for a one-way ticket and $152 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?

    Only JetBlue offers 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 Airbus A320-100/200 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Hartford to Chicago are Delta and Frontier. With an average price for the route of $442 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $229 and an overall rating of 6.2.

  • 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.

See more FAQs

Prefer to fly non-stop from Hartford to Chicago Midway Airport?

Find which airlines fly direct from Bradley Intl to Midway, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

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
DeltaOverall score based on 10818 reviews
7.9Comfort
7.4Food
8.6Crew
8.0Entertainment
8.2Boarding
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Hartford to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Hartford to Chicago found on KAYAK in the last 72 hours.
5/19Sun
1 stopFrontier
6h 55mBDL-MDW
$59
5/19Sun
1 stopFrontier
6h 55mBDL-MDW
$60
6/4Tue
1 stopFrontier
6h 46mBDL-MDW
$68
6/8Sat
1 stopFrontier
13h 40mBDL-MDW
$74
5/22Wed
1 stopFrontier
6h 26mBDL-MDW
$75
6/19Wed
1 stopDelta
4h 03mBDL-MDW
$138
6/17Mon
1 stopDelta
4h 03mBDL-MDW
$196
6/24Mon
1 stopDelta
7h 48mBDL-MDW
$204
8/18Sun
3 stops
29h 36mBDL-MDW
$252
5/24Fri
1 stopDelta
4h 26mBDL-MDW
$305

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Last minute flights from Hartford to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Hartford to Chicago that are departing in the next 10 days.
5/11Sat
multi-stopFrontier
9h 25mBDL-MDW
5/12Sun
multi-stopFrontier
13h 57mMDW-BDL
$238
5/10Fri
multi-stopFrontier
24h 25mBDL-MDW
5/12Sun
multi-stopFrontier
13h 57mMDW-BDL
$251
5/10Fri
multi-stopFrontier
24h 25mBDL-MDW
5/12Sun
multi-stopFrontier
27h 23mMDW-BDL
$258
5/9Thu
multi-stopFrontier
15h 09mBDL-MDW
5/11Sat
multi-stopFrontier
13h 15mMDW-BDL
$348
5/9Thu
multi-stopFrontier
15h 09mBDL-MDW
5/10Fri
multi-stopFrontier
17h 28mMDW-BDL
$379
5/9Thu
multi-stopFrontier
15h 09mBDL-MDW
5/10Fri
multi-stopFrontier
17h 28mMDW-BDL
$383
5/8Wed
multi-stopFrontier
25h 40mBDL-MDW
5/11Sat
multi-stopFrontier
13h 15mMDW-BDL
$401
5/7Tue
multi-stopDelta
5h 13mBDL-MDW
5/14Tue
multi-stopDelta
6h 22mMDW-BDL
$848
5/7Tue
multi-stopDelta
8h 15mBDL-MDW
5/8Wed
multi-stopDelta
6h 22mMDW-BDL
$916
5/7Tue
multi-stopDelta
8h 15mBDL-MDW
5/14Tue
multi-stopDelta
8h 36mMDW-BDL
$1,077

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Hartford - Chicago Midway Airport Flights

Departure:

Hartford (BDL)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Hartford

Cabin classes:

$525