$139+ Cheap flights from Springfield, MA, MA to Chicago (CHI)
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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Oct 21 — Oct 281
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
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.Cheapflights Tip: The best prices from Springfield to Chicago are usually found in January or December, booked 85 days in advance, depart on a Saturday or Wednesday and return on a Saturday
Cheap flight deals from Springfield to Chicago
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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 September 21, 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 September 21, 2026.
This Southwest deal was found by Cheapflights users on 9/17. 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 10/174:20 pm -
Nonstop2h 20m
Tue 10/205:30 am -
1 stop5h 45m
Deal found 9/17![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/17. 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 10/275:35 am -
2 stops9h 50m
Sat 10/318:30 am -
2 stops7h 55m
Deal found 9/17![Southwest logo]()
$288
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/107:40 pm -
1 stop4h 51m
Tue 10/137:30 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$288
This KAYAK deal was found by Cheapflights users on 9/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:25 am -
1 stop5h 59m
Mon 10/262:42 pm -
1 stop8h 17m
Deal found 9/18![JetBlue logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/293:15 pm -
1 stop17h 39m
Thu 11/59:30 am -
2 stops24h 30m
Deal found 9/18![Multiple Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 9/17. 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 10/175:00 pm -
1 stop6h 33m
Tue 10/2012:49 pm -
1 stop7h 30m
Deal found 9/17![Delta logo]()
$291
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:02 pm -
1 stop7h 32m
Sat 10/173:37 pm -
1 stop6h 59m
Deal found 9/17![American Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 9/17. 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 11/116:25 pm -
Nonstop2h 30m
Thu 11/128:00 am -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$292
This KAYAK deal was found by Cheapflights users on 9/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:25 am -
1 stop5h 59m
Sat 10/242:55 pm -
1 stop8h 03m
Deal found 9/18![JetBlue logo]()
$292
This Southwest deal was found by Cheapflights users on 9/17. 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 12/37:45 am -
Nonstop2h 30m
Sat 12/53:40 pm -
Nonstop2h 00m
Deal found 9/17![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/216:05 am -
Nonstop2h 45m
Fri 10/237:30 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$293
This Trip.com deal was found by Cheapflights users on 9/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:16 pm -
1 stop8h 43m
Wed 10/73:50 pm -
1 stop21h 31m
Deal found 9/17![Frontier logo]()
$295
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 September 21, 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 September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/293:15 pm -
1 stop17h 39m
Thu 11/59:30 am -
2 stops24h 30m
Deal found 9/18![Multiple Airlines logo]()
$290
This Southwest deal was found by Cheapflights users on 9/17. 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 10/206:25 pm -
Nonstop2h 20m
Fri 10/236:45 pm -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$296
This United Airlines deal was found by Cheapflights users on 9/21. 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 12/26:00 am -
1 stop6h 33m
Mon 12/76:20 pm -
Nonstop2h 20m
Deal found 9/21![United Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 11/235:50 pm -
1 stop7h 04m
Fri 11/277:05 am -
1 stop4h 07m
Deal found 9/21![Delta logo]()
$333
This JetBlue deal was found by Cheapflights users on 9/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
1 stop7h 45m
Mon 10/53:00 pm -
1 stop7h 14m
Deal found 9/19![JetBlue logo]()
$435
This Southwest deal was found by Cheapflights users on 9/21. 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.
Tue 11/106:25 pm -
Nonstop2h 30m
Thu 11/127:10 pm -
Nonstop2h 05m
Deal found 9/21![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Thu 12/36:00 am -
1 stop6h 33m
Mon 12/76:20 pm -
Nonstop2h 20m
Deal found 9/21![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 9/21. 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 10/211:25 pm -
Nonstop2h 20m
Sat 10/248:00 am -
Nonstop2h 10m
Deal found 9/21![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/2110:33 am -
1 stop7h 32m
Sat 10/246:15 pm -
Nonstop2h 22m
Deal found 9/21![United Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 9/21. 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.
Wed 11/255:33 pm -
1 stop6h 21m
Thu 11/266:00 am -
1 stop7h 55m
Deal found 9/21![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 9/21. 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 12/27:00 am -
2 stops8h 50m
Mon 12/76:20 pm -
Nonstop2h 00m
Deal found 9/21![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Thu 11/1210:37 am -
1 stop7h 23m
Sat 11/1410:32 am -
1 stop7h 12m
Deal found 9/20![United Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 12/285:20 am -
1 stop4h 30m
Wed 12/306:00 am -
1 stop5h 23m
Deal found 9/21![Delta logo]()
$396
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Wed 10/146:25 am -
1 stop5h 59m
Sun 10/182:55 pm -
1 stop8h 03m
Deal found 9/17![JetBlue logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/223:16 pm -
1 stop17h 38m
Sun 10/2510:20 am -
2 stops23h 40m
Deal found 9/17![Multiple Airlines logo]()
$442
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/236:00 am -
1 stop4h 37m
Mon 10/267:25 am -
Nonstop2h 18m
Deal found 9/17![United Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 9/17. 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 10/237:05 pm -
1 stop6h 20m
Mon 10/264:30 pm -
2 stops6h 25m
Deal found 9/17![Southwest logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/208:10 am -
1 stop27h 04m
Sun 10/2510:20 am -
2 stops36h 24m
Deal found 9/19![Multiple Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Wed 12/166:00 am -
1 stop6h 33m
Sat 12/192:30 pm -
Nonstop2h 18m
Deal found 9/19![United Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 9/20. 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.
Fri 10/237:05 pm -
1 stop5h 52m
Sun 10/255:27 am -
1 stop6h 26m
Deal found 9/20![Delta logo]()
$453
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:40 pm -
Nonstop2h 25m
Wed 11/186:20 pm -
Nonstop2h 05m
Deal found 9/19![Southwest logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 10/153:16 pm -
1 stop17h 43m
Mon 10/196:13 pm -
1 stop19h 48m
Deal found 9/20![Multiple Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:50 am -
2 stops8h 50m
Sun 10/257:45 am -
Nonstop2h 10m
Deal found 9/19![Southwest logo]()
$391
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/57:40 pm -
1 stop4h 52m
Wed 10/711:06 am -
Nonstop2h 23m
Deal found 9/17![United Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 9/21. 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.
Fri 10/307:25 pm -
Nonstop2h 20m
Sun 11/17:10 pm -
Nonstop2h 00m
Deal found 9/21![Southwest logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/138:10 am -
1 stop27h 04m
Fri 10/168:49 am -
2 stops12h 37m
Deal found 9/19![Multiple Airlines logo]()
$544
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 10/213:10 pm -
1 stop19h 41m
Sun 10/2510:20 am -
2 stops23h 40m
Deal found 9/20![Multiple Airlines logo]()
$548
This Southwest deal was found by Cheapflights users on 9/17. 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 11/1312:45 pm -
2 stops8h 40m
Sun 11/156:10 pm -
1 stop4h 40m
Deal found 9/17![Southwest logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/243:16 pm -
1 stop18h 36m
Fri 9/255:05 pm -
1 stop16h 51m
Deal found 9/16![Multiple Airlines logo]()
$643
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/263:10 pm -
1 stop20h 55m
Sun 9/273:53 pm -
2 stops21h 00m
Deal found 9/16![Multiple Airlines logo]()
$645
Last-minute flights from Springfield to ChicagoDiscover last-minute flight deals from Springfield to Chicago. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Chicago. Data last updated September 21, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 9/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:16 pm -
1 stop8h 43m
Wed 10/73:50 pm -
1 stop21h 31m
Deal found 9/17![Frontier logo]()
$295
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/107:40 pm -
1 stop4h 51m
Tue 10/137:30 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:02 pm -
1 stop7h 32m
Sat 10/173:37 pm -
1 stop6h 59m
Deal found 9/17![American Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 9/17. 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 10/174:20 pm -
Nonstop2h 20m
Tue 10/205:30 am -
1 stop5h 45m
Deal found 9/17![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/17. 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 10/175:00 pm -
1 stop6h 33m
Tue 10/2012:49 pm -
1 stop7h 30m
Deal found 9/17![Delta logo]()
$291
This KAYAK deal was found by Cheapflights users on 9/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:25 am -
1 stop5h 59m
Sat 10/242:55 pm -
1 stop8h 03m
Deal found 9/18![JetBlue logo]()
$292
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/216:05 am -
Nonstop2h 45m
Fri 10/237:30 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:00 pm -
Nonstop2h 48m
Sat 10/242:52 pm -
1 stop5h 31m
Deal found 9/16![American Airlines logo]()
$287
This KAYAK deal was found by Cheapflights users on 9/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:25 am -
1 stop5h 59m
Mon 10/262:42 pm -
1 stop8h 17m
Deal found 9/18![JetBlue logo]()
$289
This Southwest deal was found by Cheapflights users on 9/17. 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 10/237:05 pm -
Nonstop2h 20m
Tue 10/271:10 pm -
Nonstop2h 05m
Deal found 9/17![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 9/17. 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 10/275:35 am -
2 stops9h 50m
Sat 10/318:30 am -
2 stops7h 55m
Deal found 9/17![Southwest logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/293:15 pm -
1 stop17h 39m
Thu 11/59:30 am -
2 stops24h 30m
Deal found 9/18![Multiple Airlines logo]()
$290
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 September 21, 2026.
Search for one-way flight options from Springfield to Chicago. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Priceline deal was found by Cheapflights users on 9/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2412:26 pm -
1 stop8h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$139
This KAYAK deal was found by Cheapflights users on 9/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:25 am -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![JetBlue logo]()
$139
This KAYAK deal was found by Cheapflights users on 9/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:25 am -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![JetBlue logo]()
$140
This CheapOair deal was found by Cheapflights users on 9/17. 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.
Thu 10/156:25 am -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![JetBlue logo]()
$142
This Super.com deal was found by Cheapflights users on 9/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:28 pm -
1 stop27h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$143
This Southwest deal was found by Cheapflights users on 9/17. 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 10/275:35 am -
2 stops8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 9/17. 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 10/175:00 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$146
This Delta deal was found by Cheapflights users on 9/17. 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 10/105:14 pm -
1 stop4h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$146
This Southwest deal was found by Cheapflights users on 9/21. 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.
Tue 10/206:25 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$149
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:00 pm -
Nonstop2h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![American Airlines logo]()
$149
This CheapOair deal was found by Cheapflights users on 9/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:15 pm -
1 stop29h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$150
This CheapOair deal was found by Cheapflights users on 9/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:15 pm -
1 stop25h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$150
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 September 21, 2026.
Round-trip from | $287 (Southwest) |
|---|---|
One-way from | $139 (Priceline) |
Popular in | July |
Cheapest in | January |
Average price | $394 |
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 7,457,451 searches. Data last updated September 21, 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 Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Sat 10/10
5:23 am-10:24 am
1 stop6h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 11/10
6:25 pm-7:55 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Thu 10/22
12:38 pm-2:23 pm
Nonstop2h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Mon 10/19
7:05 pm-12:25 am
1 stop6h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Thu 10/22
5:23 am-9:32 am
1 stop5h 09m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 10/27
4:15 pm-7:25 pm
1 stop4h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 10/17
5:00 pm-10:33 pm
1 stop6h 33m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Mon 10/26
5:20 pm-10:33 pm
1 stop6h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 11/17
11:39 am-4:18 pm
1 stop5h 39m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Mon 12/21
5:20 am-8:50 am
1 stop4h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
Showing 1-10 of 58 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-MDW
BDL-ORD
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-MDW
BDL-ORD
BDL-RFD
How much does it cost to fly round-trip from Springfield to Chicago?
Airfare is below average for this route at the moment.
Springfield to Chicago flights typically cost between $329 and $472 in October.The cheapest round-trip price found within the last 5 days was $287 on Southwest (Oct 21-Oct 24).
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 September 21, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
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
Valparaiso
Hammond
Saint Joseph
Porter
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