$70+ Cheap flights from Springfield, MA, MA to Midway (MDW)
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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
Mar 6 — Mar 131
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Springfield to Midway 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Springfield to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Springfield to MidwayExplore the most affordable flight options available from Springfield to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
Explore the most affordable flight options available from Springfield to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 3/238:08 pm
BDL
- MDW
1 stop20h 25m
Frontier
Thu 3/261:24 pm
MDW
- BDL
1 stop28h 49m
Frontier
Deal found 2/2![Frontier logo]()
$287
This Southwest deal was found by Cheapflights users on 2/2. 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 2/245:30 am
BDL
- MDW
Nonstop2h 35m
Southwest
Wed 2/251:25 pm
MDW
- BDL
Nonstop1h 55m
Southwest
Deal found 2/2![Southwest logo]()
$289
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:08 pm
BDL
- MDW
1 stop21h 05m
Frontier
Sun 5/39:14 am
MDW
- BDL
1 stop9h 03m
Frontier
Deal found 2/3![Frontier logo]()
$290
This Priceline deal was found by Cheapflights users on 2/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:07 pm
BDL
- MDW
1 stop7h 24m
Frontier
Sat 5/169:14 am
MDW
- BDL
1 stop9h 03m
Frontier
Deal found 2/3![Frontier logo]()
$291
This Frontier deal was found by Cheapflights users on 2/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:52 am
BDL
- MDW
1 stop10h 35m
Frontier
Thu 2/266:25 am
MDW
- BDL
1 stop6h 07m
Frontier
Deal found 2/3![Frontier logo]()
$294
This Gotogate deal was found by Cheapflights users on 2/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/512:11 pm
BDL
- MDW
1 stop11h 08m
Frontier
Fri 2/61:00 pm
MDW
- BDL
1 stop29h 06m
Frontier
Deal found 2/2![Frontier logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 2/152:27 pm
BDL
- MDW
1 stop8h 58m
Multiple Airlines
Tue 3/107:30 am
MDW
- BDL
2 stops32h 53m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$300
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:17 pm
BDL
- MDW
1 stop21h 38m
Frontier
Sun 2/226:00 am
MDW
- BDL
1 stop6h 32m
Frontier
Deal found 2/4![Frontier logo]()
$301
This Southwest deal was found by Cheapflights users on 2/1. 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 8/117:45 am
BDL
- MDW
Nonstop2h 20m
Southwest
Sat 8/157:50 am
MDW
- BDL
Nonstop2h 15m
Southwest
Deal found 2/1![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 2/2. 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 2/285:00 am
BDL
- MDW
Nonstop2h 35m
Southwest
Sat 2/282:10 pm
MDW
- BDL
2 stops7h 35m
Southwest
Deal found 2/2![Southwest logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Fri 3/207:05 am
BDL
- MDW
2 stops16h 14m
Multiple Airlines
Tue 3/244:33 pm
MDW
- BDL
1 stop21h 32m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$305
Best flights from Springfield to MidwayDiscover carefully curated flight deals from Springfield to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Springfield to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/2. 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 3/45:30 am
BDL
- MDW
Nonstop2h 35m
Southwest
Sun 3/87:40 am
MDW
- BDL
Nonstop2h 00m
Southwest
Deal found 2/2![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 2/2. 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 2/235:30 am
BDL
- MDW
1 stop4h 24m
Delta
Wed 2/2510:49 am
MDW
- BDL
1 stop5h 52m
Delta
Deal found 2/2![Delta logo]()
$389
This Southwest deal was found by Cheapflights users on 2/1. 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 6/2312:40 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Tue 6/306:45 pm
MDW
- BDL
Nonstop2h 00m
Southwest
Deal found 2/1![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 2/2. 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 2/236:00 pm
BDL
- MDW
Nonstop2h 35m
Southwest
Tue 2/241:25 pm
MDW
- BDL
Nonstop1h 55m
Southwest
Deal found 2/2![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 2/1. 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 7/1512:40 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Tue 7/2111:50 am
MDW
- BDL
2 stops9h 55m
Southwest
Deal found 2/1![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 2/2. 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 5/139:20 am
BDL
- MDW
2 stops7h 30m
Southwest
Sat 5/1610:00 am
MDW
- BDL
2 stops9h 05m
Southwest
Deal found 2/2![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 2/2. 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 4/311:20 am
BDL
- MDW
Nonstop2h 30m
Southwest
Tue 4/71:00 pm
MDW
- BDL
1 stop5h 00m
Southwest
Deal found 2/2![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 2/2. 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 2/288:35 am
BDL
- MDW
1 stop5h 45m
Southwest
Sat 2/283:10 pm
MDW
- BDL
2 stops6h 35m
Southwest
Deal found 2/2![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 2/2. 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 5/17:45 am
BDL
- MDW
Nonstop2h 20m
Southwest
Mon 5/47:00 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 2/2![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 2/3. 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.
Thu 5/147:20 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Sun 5/176:55 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 2/3![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 2/2. 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 3/317:30 am
BDL
- MDW
Nonstop2h 30m
Southwest
Thu 4/27:45 am
MDW
- BDL
Nonstop2h 00m
Southwest
Deal found 2/2![Southwest logo]()
$388
Last-minute flights from Springfield to MidwayDiscover last-minute flight deals from Springfield to Midway. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Midway. Data last updated February 4, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 2/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/512:11 pm
BDL
- MDW
1 stop11h 08m
Frontier
Fri 2/61:00 pm
MDW
- BDL
1 stop29h 06m
Frontier
Deal found 2/2![Frontier logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 2/152:27 pm
BDL
- MDW
1 stop8h 58m
Multiple Airlines
Tue 3/107:30 am
MDW
- BDL
2 stops32h 53m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$300
This Priceline deal was found by Cheapflights users on 2/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:27 pm
BDL
- MDW
1 stop9h 10m
Frontier
Sun 2/226:00 am
MDW
- BDL
1 stop6h 32m
Frontier
Deal found 2/2![Frontier logo]()
$315
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:17 pm
BDL
- MDW
1 stop21h 38m
Frontier
Sun 2/226:00 am
MDW
- BDL
1 stop6h 32m
Frontier
Deal found 2/3![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 2/222:27 pm
BDL
- MDW
1 stop8h 58m
Multiple Airlines
Mon 2/237:25 pm
MDW
- BDL
1 stop23h 40m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 2/2. 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 2/245:30 am
BDL
- MDW
Nonstop2h 35m
Southwest
Wed 2/251:25 pm
MDW
- BDL
Nonstop1h 55m
Southwest
Deal found 2/2![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 2/2. 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.
Tue 2/246:00 am
BDL
- MDW
1 stop6h 59m
Delta
Tue 2/246:20 pm
MDW
- BDL
1 stop4h 19m
Delta
Deal found 2/2![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 2/3. 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 2/256:00 am
BDL
- MDW
2 stops8h 55m
Southwest
Wed 2/253:15 pm
MDW
- BDL
1 stop6h 05m
Southwest
Deal found 2/3![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 2/2. 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 2/285:00 am
BDL
- MDW
Nonstop2h 35m
Southwest
Sat 2/282:10 pm
MDW
- BDL
2 stops7h 35m
Southwest
Deal found 2/2![Southwest logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 3/238:08 pm
BDL
- MDW
1 stop20h 25m
Frontier
Thu 3/261:24 pm
MDW
- BDL
1 stop28h 49m
Frontier
Deal found 2/2![Frontier logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/318:05 am
BDL
- MDW
2 stops13h 49m
Multiple Airlines
Thu 4/29:20 am
MDW
- BDL
1 stop10h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$312
One-way flights from Springfield to MidwaySearch for one-way flight options from Springfield to Midway. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Springfield to Midway. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:19 am
BDL
- MDW
1 stop29h 07m
Frontier
Deal found 2/2![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 2/192:27 pm
BDL
- MDW
1 stop9h 10m
Frontier
Deal found 2/3![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 2/262:27 pm
BDL
- MDW
1 stop29h 11m
Frontier
Deal found 2/3![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Mon 3/98:08 pm
BDL
- MDW
1 stop23h 05m
Frontier
Deal found 2/3![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 5/38:08 pm
BDL
- MDW
1 stop12h 56m
Frontier
Deal found 2/3![Frontier logo]()
$84
This Frontier deal was found by Cheapflights users on 2/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:07 pm
BDL
- MDW
1 stop10h 12m
Frontier
Deal found 2/3![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Mon 3/168:08 pm
BDL
- MDW
1 stop23h 05m
Frontier
Deal found 2/3![Frontier logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 3/53:40 pm
BDL
- MDW
1 stop7h 49m
Frontier
Deal found 2/3![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Mon 3/238:08 pm
BDL
- MDW
2 stops17h 54m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Tue 2/249:49 am
BDL
- MDW
2 stops34h 18m
Frontier
Deal found 2/3![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 4/268:08 pm
BDL
- MDW
1 stop12h 56m
Frontier
Deal found 2/3![Frontier logo]()
$100
Find flight deals from Springfield to Midway
Keep the following information in mind while searching for Springfield to Midway flight deals. Data was last updated February 4, 2026.
Round-trip from | $287 (Kiwi.com) |
|---|---|
One-way from | $70 (Mytrip) |
Popular in | February |
Cheapest in | August |
Average price | $607 |
Cheapflights Fare Finder
Customize your flight search to find flights from Springfield to Midway 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 February 4, 2026.
Use the filters below to find and compare flights from Springfield to Chicago Midway Airport that are best for you.
Fly from
Springfield
Fly to
Midway
Route
Depart
Return
Price
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Wed 3/4
5:30 am-7:05 am
Nonstop2h 35m
Chicago Midway
Sun 3/8
7:40 am-10:40 am
Nonstop2h 00m
$351
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Tue 6/23
12:40 pm-2:05 pm
Nonstop2h 25m
Chicago Midway
Tue 6/30
6:45 pm-9:45 pm
Nonstop2h 00m
$363
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Mon 2/23
6:00 pm-7:35 pm
Nonstop2h 35m
Chicago Midway
Tue 2/24
1:25 pm-4:20 pm
Nonstop1h 55m
$369
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Wed 7/15
12:40 pm-2:05 pm
Nonstop2h 25m
Chicago Midway
Tue 7/21
11:50 am-10:45 pm
2 stops9h 55m
$378
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Wed 5/13
9:20 am-3:50 pm
2 stops7h 30m
Chicago Midway
Sat 5/16
10:00 am-8:05 pm
2 stops9h 05m
$379
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Fri 4/3
11:20 am-12:50 pm
Nonstop2h 30m
Chicago Midway
Tue 4/7
1:00 pm-7:00 pm
1 stop5h 00m
$384
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sat 2/28
8:35 am-1:20 pm
1 stop5h 45m
Chicago Midway
Sat 2/28
3:10 pm-10:45 pm
2 stops6h 35m
$384
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Fri 5/1
7:45 am-9:05 am
Nonstop2h 20m
Chicago Midway
Mon 5/4
7:00 pm-10:05 pm
Nonstop2h 05m
$387
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Thu 5/14
7:20 pm-8:45 pm
Nonstop2h 25m
Chicago Midway
Sun 5/17
6:55 pm-10:00 pm
Nonstop2h 05m
$387
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Tue 3/31
7:30 am-9:00 am
Nonstop2h 30m
Chicago Midway
Thu 4/2
7:45 am-10:45 am
Nonstop2h 00m
$388
Showing 1-10 of 20 results
Best time to book a flight from Springfield to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Springfield with our price prediction graph.
BDL-MDW
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 Springfield to Chicago Midway Airport
SFY-MDW
BDL-MDW
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated February 4, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Springfield to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Springfield to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Popular flights
Top destinations