$148+ Cheap flights from Midway (MDW) to Hartford (BDL)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Sep 6 — Sep 131
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
Cheapest
Best
Last-minute
One-way
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 August 7, 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 August 7, 2026.
This Southwest deal was found by Cheapflights users on 8/3. 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 9/53:25 pm -
Nonstop2h 05m
Sun 9/66:15 pm -
Nonstop2h 20m
Deal found 8/3![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/4. 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 9/117:10 pm -
Nonstop2h 10m
Mon 9/146:20 pm -
Nonstop2h 20m
Deal found 8/4![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:39 pm -
1 stop6h 19m
Sun 9/61:09 pm -
1 stop4h 50m
Deal found 8/4![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 8/7. 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.
Thu 9/101:10 pm -
Nonstop2h 05m
Tue 9/1512:45 pm -
Nonstop2h 20m
Deal found 8/7![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:30 pm -
1 stop6h 29m
Tue 9/155:55 pm -
1 stop5h 49m
Deal found 8/7![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 8/7. 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.
Thu 9/108:45 am -
Nonstop2h 15m
Wed 9/1612:40 pm -
1 stop4h 10m
Deal found 8/7![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 8/4. 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 9/41:10 pm -
Nonstop2h 05m
Sat 9/53:50 pm -
Nonstop2h 25m
Deal found 8/4![Southwest logo]()
$328
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 August 7, 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 August 7, 2026.
This Southwest deal was found by Cheapflights users on 8/4. 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.
Thu 10/157:50 am -
Nonstop2h 10m
Sat 10/174:20 pm -
Nonstop2h 20m
Deal found 8/4![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:31 pm -
1 stop4h 59m
Sat 10/105:23 am -
1 stop4h 54m
Deal found 8/5![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 8/4. 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.
Thu 8/271:10 pm -
Nonstop2h 05m
Sat 8/2910:05 am -
1 stop8h 05m
Deal found 8/4![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:42 pm -
1 stop4h 09m
Sun 9/61:09 pm -
1 stop4h 50m
Deal found 8/5![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 9/269:20 am -
2 stops9h 15m
Mon 9/286:20 pm -
Nonstop2h 20m
Deal found 8/5![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 8/3. 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.
Mon 9/78:45 am -
Nonstop2h 15m
Sat 9/126:30 am -
2 stops11h 35m
Deal found 8/3![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 8/4. 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 9/41:05 pm -
2 stops8h 10m
Sun 9/66:15 pm -
Nonstop2h 20m
Deal found 8/4![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 10/311:25 am -
2 stops9h 20m
Sun 10/47:20 pm -
Nonstop2h 20m
Deal found 8/5![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2212:45 pm -
Nonstop2h 00m
Wed 11/257:20 am -
Nonstop2h 30m
Deal found 8/6![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 8/5. 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.
Fri 10/166:45 pm -
Nonstop2h 05m
Sun 10/1812:35 pm -
Nonstop2h 20m
Deal found 8/5![Southwest logo]()
$397
Last-minute flights from Midway to HartfordDiscover last-minute flight deals from Midway to Hartford. Data last updated August 7, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hartford. Data last updated August 7, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/4. 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 9/47:10 pm -
Nonstop2h 10m
Sun 9/66:15 pm -
Nonstop2h 20m
Deal found 8/4![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 8/3. 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 9/53:25 pm -
Nonstop2h 05m
Sun 9/66:15 pm -
Nonstop2h 20m
Deal found 8/3![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:39 pm -
1 stop6h 19m
Sun 9/61:09 pm -
1 stop4h 50m
Deal found 8/4![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:45 pm -
1 stop5h 06m
Mon 9/75:30 am -
1 stop4h 47m
Deal found 8/5![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 8/4. 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 9/117:10 pm -
Nonstop2h 10m
Mon 9/146:20 pm -
Nonstop2h 20m
Deal found 8/4![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 9/197:50 am -
Nonstop2h 15m
Sat 9/267:55 am -
Nonstop2h 20m
Deal found 8/5![Southwest logo]()
$315
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 August 7, 2026.
Search for one-way flight options from Midway to Hartford. Find affordable one-way fares based on user searches. Data last updated August 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:25 am -
2 stops9h 43m
Deal found 8/6![Multiple Airlines logo]()
$148
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:52 pm -
1 stop5h 33m
Deal found 8/6![Delta logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:25 am -
2 stops9h 43m
Deal found 8/6![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Sat 11/712:03 pm -
2 stops30h 58m
Deal found 8/7![Frontier logo]()
$157
This Southwest deal was found by Cheapflights users on 8/4. 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 8/258:45 am -
Nonstop2h 15m
Deal found 8/4![Southwest logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Thu 10/812:03 pm -
2 stops34h 41m
Deal found 8/5![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:25 am -
2 stops10h 53m
Deal found 8/6![Multiple Airlines logo]()
$164
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:05 am -
1 stop5h 43m
Deal found 8/5![Delta logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Tue 9/111:50 am -
2 stops30h 02m
Deal found 8/5![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/4. 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.
Wed 8/2611:50 am -
3 stops34h 21m
Deal found 8/4![Multiple Airlines logo]()
$172
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 August 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (Southwest) |
One-way from | $148 (Kiwi.com) |
Popular in | July |
Cheapest in | October |
Average price | $488 |
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 2,558,603 searches. Data last updated August 7, 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
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Thu 10/15
7:50 am-11:00 am
Nonstop2h 10m
Hartford Bradley Intl
Sat 10/17
4:20 pm-5:40 pm
Nonstop2h 20m
$315
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Thu 8/27
1:10 pm-4:15 pm
Nonstop2h 05m
Hartford Bradley Intl
Sat 8/29
10:05 am-5:10 pm
1 stop8h 05m
$325
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Sat 9/26
9:20 am-7:35 pm
2 stops9h 15m
Hartford Bradley Intl
Mon 9/28
6:20 pm-7:40 pm
Nonstop2h 20m
$330
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Mon 9/7
8:45 am-12:00 pm
Nonstop2h 15m
Hartford Bradley Intl
Sat 9/12
6:30 am-5:05 pm
2 stops11h 35m
$330
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Wed 10/7
5:31 pm-11:30 pm
1 stop4h 59m
Hartford Bradley Intl
Sat 10/10
5:23 am-9:17 am
1 stop4h 54m
$335
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Fri 9/4
1:05 pm-10:15 pm
2 stops8h 10m
Hartford Bradley Intl
Sun 9/6
6:15 pm-7:35 pm
Nonstop2h 20m
$343
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Fri 9/4
6:42 pm-11:51 pm
1 stop4h 09m
Hartford Bradley Intl
Sun 9/6
1:09 pm-4:59 pm
1 stop4h 50m
$348
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Sat 10/3
11:25 am-9:45 pm
2 stops9h 20m
Hartford Bradley Intl
Sun 10/4
7:20 pm-8:40 pm
Nonstop2h 20m
$380
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Sun 11/22
12:45 pm-3:45 pm
Nonstop2h 00m
Hartford Bradley Intl
Wed 11/25
7:20 am-8:50 am
Nonstop2h 30m
$393
Quickest round-trip
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Fri 10/16
6:45 pm-9:50 pm
Nonstop2h 05m
Hartford Bradley Intl
Sun 10/18
12:35 pm-1:55 pm
Nonstop2h 20m
$397
Showing 1-10 of 19 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 August.
| 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 August 7, 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.
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
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 locationsUncasville
West Springfield
New Britain
Southington
Enfield
Windsor Locks
Cromwell
Newington
Windsor
Farmington
East Hartford
Westfield
Rocky Hill
Northampton
Glastonbury
Meriden
Lee
West Hartford
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Midway and Hartford flights
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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 2,558,603 searches. Data last updated August 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$403 | FlexibilityNo cancel fee | On-time63% |