$159+ Cheap flights from Midway (MDW) to Hartford (BDL)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Oct 8 — Oct 151
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Hartford with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Hartford
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Best
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Cheapest flights from Midway to HartfordExplore the most affordable flight options available from Midway to Hartford. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 8, 2026.
Explore the most affordable flight options available from Midway to Hartford. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 8, 2026.
This CheapOair deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop13h 49m
Fri 11/2712:26 pm -
1 stop8h 21m
Deal found 9/6![Frontier logo]()
$296
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:00 am -
Nonstop2h 10m
Wed 10/146:25 pm -
Nonstop2h 20m
Deal found 9/8![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:25 pm -
Nonstop2h 10m
Sat 10/38:10 am -
Nonstop2h 20m
Deal found 9/3![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:45 pm -
Nonstop2h 10m
Fri 10/307:25 pm -
Nonstop2h 20m
Deal found 9/8![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:44 pm -
1 stop3h 48m
Mon 10/125:23 am -
1 stop5h 09m
Deal found 9/3![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:20 pm -
Nonstop2h 00m
Sat 11/216:50 pm -
Nonstop2h 25m
Deal found 9/8![Southwest logo]()
$344
Best flights from Midway to HartfordDiscover carefully curated flight deals from Midway to Hartford that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 8, 2026.
Discover carefully curated flight deals from Midway to Hartford that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 8, 2026.
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:20 am -
2 stops6h 10m
Mon 11/97:25 am -
Nonstop2h 30m
Deal found 9/3![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:44 pm -
1 stop3h 48m
Sun 10/2512:57 pm -
1 stop6h 03m
Deal found 9/3![Delta logo]()
$410
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:35 am -
2 stops5h 15m
Sat 10/37:05 am -
1 stop4h 35m
Deal found 9/3![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:40 am -
2 stops7h 05m
Sun 10/117:35 am -
Nonstop2h 20m
Deal found 9/3![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:45 pm -
Nonstop2h 10m
Mon 10/126:50 am -
Nonstop2h 20m
Deal found 9/7![Southwest logo]()
$399
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:50 am -
Nonstop2h 00m
Tue 12/18:40 am -
1 stop7h 00m
Deal found 9/5![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:20 pm -
Nonstop2h 00m
Sun 11/227:25 am -
Nonstop2h 30m
Deal found 9/4![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:45 am -
Nonstop2h 10m
Wed 10/146:25 pm -
Nonstop2h 20m
Deal found 9/7![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:00 am -
Nonstop2h 10m
Sun 10/412:35 pm -
Nonstop2h 20m
Deal found 9/4![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:45 pm -
1 stop6h 55m
Sun 10/47:35 am -
Nonstop2h 20m
Deal found 9/4![Southwest logo]()
$427
Last-minute flights from Midway to HartfordDiscover last-minute flight deals from Midway to Hartford. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hartford. Data last updated September 8, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:25 pm -
Nonstop2h 10m
Sat 10/31:10 pm -
1 stop4h 00m
Deal found 9/3![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:00 am -
Nonstop2h 10m
Wed 10/146:25 pm -
Nonstop2h 20m
Deal found 9/8![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:44 pm -
1 stop3h 48m
Mon 10/125:23 am -
1 stop5h 09m
Deal found 9/3![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:04 am -
1 stop5h 49m
Thu 10/155:23 am -
1 stop5h 09m
Deal found 9/8![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:44 pm -
1 stop3h 48m
Fri 10/165:20 pm -
1 stop6h 13m
Deal found 9/8![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:45 pm -
Nonstop2h 10m
Fri 10/307:25 pm -
Nonstop2h 20m
Deal found 9/8![Southwest logo]()
$335
One-way flights from Midway to HartfordSearch for one-way flight options from Midway to Hartford. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
Search for one-way flight options from Midway to Hartford. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:45 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:00 am -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/141:00 pm -
1 stop3h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:44 pm -
1 stop3h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$179
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:05 pm -
2 stops8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:53 am -
2 stops26h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:25 am -
2 stops15h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:25 am -
2 stops16h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:21 am -
2 stops31h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:16 am -
3 stops35h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$191
Find flight deals from Midway to Hartford
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Hartford (BDL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (CheapOair) |
One-way from | $159 (Southwest) |
Popular in | July |
Cheapest in | November |
Average price | $365 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Hartford that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 8, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Hartford that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Fri 12/4
6:20 pm-9:20 pm
Nonstop2h 00m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Sat 11/14
7:50 am-3:10 pm
1 stop6h 20m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$206
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Tue 10/6
6:04 am-12:53 pm
1 stop5h 49m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$210
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Sat 10/3
4:30 pm-11:59 pm
1 stop6h 29m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$210
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Thu 10/8
6:44 pm-11:32 pm
1 stop3h 48m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$210
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Mon 11/9
5:13 pm-11:59 pm
1 stop5h 46m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$210
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Thu 10/8
8:55 pm-8:10 am
1 stop10h 15m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$215
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Tue 10/6
7:45 am-5:45 pm
2 stops9h 00m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$215
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Wed 12/2
5:30 pm-11:43 pm
1 stop5h 13m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$216
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Sat 10/31
6:44 pm-11:32 pm
1 stop3h 48m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$216
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Midway to Hartford
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Hartford in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Hartford flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Hartford flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Hartford flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Hartford flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Hartford flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Hartford
Have a flexible travel schedule? Discover the best time to fly to Hartford from Midway with our price prediction graph.
MDW-BDL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Hartford
Reviews of airlines servicing Hartford
Get insights into the airlines that provide service to Hartford. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hartford. Reviews last updated September 8, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Hartford, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Related info for your journey
Find useful and relevant information for your journey from Midway to Hartford. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Hartford?
Book flights to Hartford if you plan to visit one of these locationsWest Springfield
Uncasville
New Britain
Southington
Enfield
Windsor Locks
Cromwell
Newington
Windsor
Farmington
Westfield
Meriden
Rocky Hill
Northampton
Glastonbury
East Hartford
West Hartford
Lee
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Midway and Hartford flights
Browse other Midway and Hartford flight options. Last updated on September 8, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Hartford
Discover the top airline that operate flights from Midway to Hartford. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$423 | FlexibilityNo cancel fee | On-time63% |