$180+ Cheap flights from Springfield, MA, MA to Chicago (CHI)
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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Jul 23 — Jul 301
Round-trip
1 adult, Economy
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Find cheap flights from Springfield to Chicago 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.Cheapflights Tip: The best prices from Springfield to Chicago are usually found in January or October, booked 85 days in advance, depart on a Wednesday or Tuesday and return on a Thursday
Cheap flight deals from Springfield to Chicago
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Best
Last-minute
One-way
Cheapest flights from Springfield to ChicagoExplore the most affordable flight options available from Springfield to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 23, 2026.
Explore the most affordable flight options available from Springfield to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 23, 2026.
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:09 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Sat 7/256:12 pm
ORD
- BDL
1 stop4h 47m
United Airlines
Deal found 6/18![United Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/148:10 am
BDL
- ORD
2 stops16h 00m
Multiple Airlines
Tue 7/285:13 pm
ORD
- BDL
1 stop17h 19m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 6/22. 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 8/126:00 am
BDL
- MDW
2 stops6h 50m
Southwest
Sat 8/159:05 am
MDW
- BDL
1 stop5h 05m
Southwest
Deal found 6/22![Southwest logo]()
$352
This Travelocity deal was found by Cheapflights users on 6/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:42 pm
BDL
- ORD
1 stop10h 45m
Multiple Airlines
Fri 10/301:00 pm
ORD
- BDL
1 stop9h 33m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 6/18. 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 10/246:00 am
BDL
- MDW
2 stops9h 05m
Southwest
Mon 10/268:35 am
MDW
- BDL
2 stops5h 00m
Southwest
Deal found 6/18![Southwest logo]()
$353
This United Airlines deal was found by Cheapflights users on 6/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:37 am
BDL
- ORD
1 stop7h 18m
United Airlines
Sun 11/87:15 am
ORD
- BDL
Nonstop2h 10m
United Airlines
Deal found 6/19![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 6/18. 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 9/66:15 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Tue 9/88:40 am
MDW
- BDL
2 stops7h 30m
Southwest
Deal found 6/18![Southwest logo]()
$354
This JetBlue deal was found by Cheapflights users on 6/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/275:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Fri 7/315:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 6/23![JetBlue logo]()
$354
This Southwest deal was found by Cheapflights users on 6/20. 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 7/294:00 pm
BDL
- MDW
2 stops8h 15m
Southwest
Sat 8/11:15 pm
MDW
- BDL
2 stops9h 10m
Southwest
Deal found 6/20![Southwest logo]()
$355
This Sun Country Air deal was found by Cheapflights users on 6/22. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:41 pm
BDL
- ORD
1 stop23h 23m
Sun Country Air
Sat 7/116:05 pm
ORD
- BDL
1 stop15h 52m
Sun Country Air
Deal found 6/22![Sun Country Air logo]()
$355
This Priceline deal was found by Cheapflights users on 6/20. 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 7/32:10 pm
BDL
- ORD
1 stop10h 19m
Frontier
Sun 7/512:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Deal found 6/20![Frontier logo]()
$356
This Southwest deal was found by Cheapflights users on 6/21. 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 7/294:00 pm
BDL
- MDW
1 stop6h 40m
Southwest
Thu 7/307:45 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 6/21![Southwest logo]()
$357
Best flights from Springfield to ChicagoDiscover carefully curated flight deals from Springfield to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 23, 2026.
Discover carefully curated flight deals from Springfield to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 23, 2026.
This Southwest deal was found by Cheapflights users on 6/22. 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 8/275:00 pm
BDL
- MDW
1 stop6h 20m
Southwest
Mon 8/318:10 am
MDW
- BDL
2 stops8h 30m
Southwest
Deal found 6/22![Southwest logo]()
$352
This United Airlines deal was found by Cheapflights users on 6/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:50 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Mon 9/216:15 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 6/20![United Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 6/20. 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.
Sun 8/95:16 pm
BDL
- MDW
1 stop6h 20m
Delta
Wed 8/126:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Deal found 6/20![Delta logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 8/612:25 pm
BDL
- RFD
2 stops20h 24m
Multiple Airlines
Mon 8/106:26 pm
RFD
- BDL
1 stop29h 15m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$374
This JetBlue deal was found by Cheapflights users on 6/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Mon 7/135:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 6/22![JetBlue logo]()
$446
This Southwest deal was found by Cheapflights users on 6/18. 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 7/185:55 pm
BDL
- MDW
Nonstop2h 35m
Southwest
Sat 7/257:45 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 6/18![Southwest logo]()
$361
This United Airlines deal was found by Cheapflights users on 6/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:05 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Sun 10/117:30 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 6/19![United Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 6/19. 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 8/15:30 am
BDL
- MDW
1 stop4h 43m
Delta
Sat 8/86:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Deal found 6/19![Delta logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 8/263:20 pm
BDL
- RFD
1 stop20h 44m
Multiple Airlines
Sun 8/3010:44 am
RFD
- BDL
2 stops25h 01m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 6/18. 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 7/277:10 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Tue 7/287:50 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 6/18![Southwest logo]()
$361
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:11 pm
BDL
- ORD
1 stop4h 30m
United Airlines
Mon 10/127:30 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 6/21![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 6/21. 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.
Thu 9/175:30 am
BDL
- MDW
1 stop4h 37m
Delta
Sun 9/205:11 pm
MDW
- BDL
1 stop5h 47m
Delta
Deal found 6/21![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 6/22. 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 7/226:30 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Sat 7/256:30 am
MDW
- BDL
1 stop7h 30m
Southwest
Deal found 6/22![Southwest logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/2912:29 pm
BDL
- RFD
2 stops23h 08m
Multiple Airlines
Sat 8/19:05 am
RFD
- BDL
1 stop11h 48m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$420
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:47 am
BDL
- ORD
Nonstop2h 53m
United Airlines
Fri 7/317:00 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Deal found 6/21![United Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 6/22. 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 8/153:30 pm
BDL
- MDW
1 stop6h 00m
Southwest
Mon 8/175:30 am
MDW
- BDL
2 stops6h 30m
Southwest
Deal found 6/22![Southwest logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 7/186:15 am
BDL
- RFD
2 stops29h 22m
Multiple Airlines
Wed 7/2211:19 am
RFD
- BDL
1 stop11h 52m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 6/22. 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 7/292:35 pm
BDL
- MDW
2 stops9h 05m
Southwest
Fri 7/312:40 pm
MDW
- BDL
2 stops8h 40m
Southwest
Deal found 6/22![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:00 am
BDL
- ORD
1 stop4h 36m
United Airlines
Mon 8/36:10 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 6/21![United Airlines logo]()
$415
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:00 am
BDL
- ORD
1 stop6h 53m
United Airlines
Sun 8/167:15 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 6/22![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 6/22. 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 7/157:55 am
BDL
- MDW
Nonstop2h 20m
Southwest
Wed 7/227:50 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 6/22![Southwest logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 9/178:55 pm
BDL
- RFD
1 stop12h 57m
Multiple Airlines
Sun 9/203:53 pm
RFD
- BDL
2 stops21h 00m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$499
This Southwest deal was found by Cheapflights users on 6/22. 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 9/176:20 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Sun 9/207:55 am
MDW
- BDL
2 stops8h 15m
Southwest
Deal found 6/22![Southwest logo]()
$381
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:09 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Fri 7/247:00 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Deal found 6/21![United Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 7/37:11 pm
BDL
- RFD
2 stops15h 04m
Multiple Airlines
Fri 7/107:50 pm
RFD
- BDL
1 stop22h 35m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$504
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2012:12 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Wed 7/226:10 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 6/18![United Airlines logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/275:40 pm
BDL
- RFD
2 stops18h 43m
Multiple Airlines
Mon 8/317:04 pm
RFD
- BDL
1 stop18h 46m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$509
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
BDL
- ORD
1 stop4h 38m
United Airlines
Sun 8/166:19 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 6/22![United Airlines logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/186:15 am
BDL
- RFD
2 stops29h 22m
Multiple Airlines
Sat 7/259:05 am
RFD
- BDL
1 stop11h 48m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$524
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
BDL
- ORD
1 stop4h 36m
United Airlines
Mon 8/36:10 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 6/21![United Airlines logo]()
$473
Last-minute flights from Springfield to ChicagoDiscover last-minute flight deals from Springfield to Chicago. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Chicago. Data last updated June 23, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 6/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:54 pm
BDL
- ORD
1 stop11h 25m
Frontier
Fri 6/264:59 pm
ORD
- BDL
1 stop25h 21m
Frontier
Deal found 6/22![Frontier logo]()
$360
This Sun Country Air deal was found by Cheapflights users on 6/22. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:41 pm
BDL
- ORD
1 stop23h 23m
Sun Country Air
Sat 7/116:05 pm
ORD
- BDL
1 stop15h 52m
Sun Country Air
Deal found 6/22![Sun Country Air logo]()
$355
This Priceline deal was found by Cheapflights users on 6/20. 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 7/32:10 pm
BDL
- ORD
1 stop10h 19m
Frontier
Sun 7/512:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Deal found 6/20![Frontier logo]()
$356
This Booking.com deal was found by Cheapflights users on 6/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/51:42 pm
BDL
- ORD
1 stop10h 45m
Frontier
Thu 7/912:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Deal found 6/22![Frontier logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/148:10 am
BDL
- ORD
2 stops16h 00m
Multiple Airlines
Tue 7/285:13 pm
ORD
- BDL
1 stop17h 19m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$351
This Travelocity deal was found by Cheapflights users on 6/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:42 pm
BDL
- ORD
1 stop10h 45m
Multiple Airlines
Fri 10/301:00 pm
ORD
- BDL
1 stop9h 33m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 6/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1812:12 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Mon 7/203:53 pm
ORD
- BDL
1 stop7h 06m
United Airlines
Deal found 6/20![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 6/18. 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 7/184:30 pm
BDL
- MDW
1 stop6h 45m
Delta
Tue 7/215:10 pm
MDW
- BDL
1 stop5h 44m
Delta
Deal found 6/18![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:09 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Sat 7/256:12 pm
ORD
- BDL
1 stop4h 47m
United Airlines
Deal found 6/18![United Airlines logo]()
$349
This JetBlue deal was found by Cheapflights users on 6/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/275:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Fri 7/315:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 6/23![JetBlue logo]()
$354
This Southwest deal was found by Cheapflights users on 6/20. 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 7/294:00 pm
BDL
- MDW
2 stops8h 15m
Southwest
Sat 8/11:15 pm
MDW
- BDL
2 stops9h 10m
Southwest
Deal found 6/20![Southwest logo]()
$355
This Southwest deal was found by Cheapflights users on 6/21. 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 7/294:00 pm
BDL
- MDW
1 stop6h 40m
Southwest
Thu 7/307:45 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 6/21![Southwest logo]()
$357
One-way flights from Springfield to ChicagoSearch for one-way flight options from Springfield to Chicago. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
Search for one-way flight options from Springfield to Chicago. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Delta deal was found by Cheapflights users on 6/22. 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 7/184:30 pm
BDL
- MDW
1 stop6h 45m
Delta
Deal found 6/22![Delta logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/207:02 am
BDL
- ORD
2 stops17h 06m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/207:02 am
BDL
- RFD
2 stops9h 07m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$181
This Southwest deal was found by Cheapflights users on 6/22. 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 7/226:30 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Deal found 6/22![Southwest logo]()
$181
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/14:55 pm
BDL
- ORD
Nonstop2h 49m
United Airlines
Deal found 6/22![United Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/77:25 am
BDL
- ORD
2 stops29h 50m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/156:00 am
BDL
- RFD
2 stops29h 37m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$184
This Priceline deal was found by Cheapflights users on 6/20. 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 6/2612:38 pm
BDL
- ORD
1 stop11h 41m
Frontier
Deal found 6/20![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/227:32 pm
BDL
- MDW
2 stops16h 23m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$185
This United Airlines deal was found by Cheapflights users on 6/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1812:12 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 6/23![United Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 9/186:00 am
BDL
- MDW
2 stops40h 58m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/227:32 pm
BDL
- ORD
2 stops42h 48m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$186
Find flight deals from Springfield to Chicago
Keep the following information in mind while searching for Springfield to Chicago flight deals. Data was last updated June 23, 2026.
Round-trip from | $349 (United Airlines) |
|---|---|
One-way from | $180 (Delta) |
Popular in | June |
Cheapest in | January |
Average price | $436 |
Cheapflights Fare Finder
Customize your flight search to find flights from Springfield to Chicago 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 June 23, 2026.
Use the filters below to find and compare flights from Springfield to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Thu 8/27
5:00 pm-10:20 pm
1 stop6h 20m
Chicago Midway
Mon 8/31
8:10 am-5:40 pm
2 stops8h 30m
$352
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sat 7/18
5:55 pm-7:30 pm
Nonstop2h 35m
Chicago Midway
Sat 7/25
7:45 am-10:55 am
Nonstop2h 10m
$361
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Mon 7/27
7:10 pm-8:40 pm
Nonstop2h 30m
Chicago Midway
Tue 7/28
7:50 am-11:00 am
Nonstop2h 10m
$361
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Fri 9/18
4:50 pm-6:35 pm
Nonstop2h 45m
Chicago O'Hare Intl
Mon 9/21
6:15 pm-9:38 pm
Nonstop2h 23m
$366
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Thu 10/8
6:05 am-7:50 am
Nonstop2h 45m
Chicago O'Hare Intl
Sun 10/11
7:30 am-10:53 am
Nonstop2h 23m
$366
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sun 8/9
5:16 pm-10:36 pm
1 stop6h 20m
Chicago Midway
Wed 8/12
6:42 pm-11:51 pm
1 stop4h 09m
$367
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Wed 7/22
6:30 pm-8:00 pm
Nonstop2h 30m
Chicago Midway
Sat 7/25
6:30 am-3:00 pm
1 stop7h 30m
$371
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sat 8/15
3:30 pm-8:30 pm
1 stop6h 00m
Chicago Midway
Mon 8/17
5:30 am-1:00 pm
2 stops6h 30m
$372
HartfordChicago
BDL - RFD
BDLRFD
Hartford Bradley Intl
Thu 8/6
12:25 pm-7:49 am
2 stops20h 24m
Chicago Greater Rockford
Mon 8/10
6:26 pm-12:41 am
1 stop29h 15m
$374
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Wed 10/7
3:11 pm-6:41 pm
1 stop4h 30m
Chicago O'Hare Intl
Mon 10/12
7:30 am-10:53 am
Nonstop2h 23m
$374
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Springfield to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Springfield with our price prediction graph.
BDL-ORD
BDL-MDW
BDL-RFD
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
SFY-CHI
BDL-ORD
BDL-MDW
BDL-RFD
How much does it cost to fly round-trip from Springfield to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 23, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Springfield to Chicago. 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.
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Springfield to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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