$147+ Cheap flights from Chicago (CHI) to Springfield, MA, MA
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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Springfield 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 Chicago to Springfield are usually found in September or October, booked 69 days in advance, depart on a Saturday or Thursday and return on a Wednesday
Cheap flight deals from Chicago to Springfield
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Best
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One-way
Cheapest flights from Chicago to SpringfieldExplore the most affordable flight options available from Chicago to Springfield. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
Explore the most affordable flight options available from Chicago to Springfield. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
This United Airlines deal was found by Cheapflights users on 7/30. 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 8/247:15 am -
Nonstop2h 23m
Mon 8/314:50 pm -
Nonstop2h 45m
Deal found 7/30![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 7/30. 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 8/251:00 pm -
Nonstop2h 05m
Sat 8/293:50 pm -
Nonstop2h 25m
Deal found 7/30![Southwest logo]()
$277
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:56 am -
Nonstop2h 26m
Sun 9/67:00 am -
Nonstop2h 53m
Deal found 8/1![American Airlines logo]()
$279
This CheapOair deal was found by Cheapflights users on 7/31. 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 9/37:44 pm -
1 stop14h 48m
Mon 9/712:27 pm -
1 stop11h 41m
Deal found 7/31![Frontier logo]()
$280
This Frontier deal was found by Cheapflights users on 8/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:26 am -
1 stop9h 35m
Sun 11/158:55 pm -
1 stop12h 26m
Deal found 8/2![Frontier logo]()
$282
This Faresmojo deal was found by Cheapflights users on 8/2. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:00 am -
1 stop10h 55m
Sun 11/297:50 am -
1 stop7h 40m
Deal found 8/2![JetBlue logo]()
$283
This JetBlue deal was found by Cheapflights users on 7/30. 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 8/135:27 pm -
1 stop5h 53m
Mon 8/175:07 pm -
1 stop7h 37m
Deal found 7/30![JetBlue logo]()
$285
This Priceline deal was found by Cheapflights users on 8/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am -
1 stop11h 03m
Tue 9/11:42 pm -
1 stop10h 45m
Deal found 8/1![Frontier logo]()
$288
This JetBlue deal was found by Cheapflights users on 7/30. 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 8/245:27 pm -
1 stop5h 53m
Thu 8/275:07 pm -
1 stop7h 37m
Deal found 7/30![JetBlue logo]()
$289
This Frontier deal was found by Cheapflights users on 7/30. 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 11/29:26 am -
1 stop9h 35m
Sun 11/88:55 pm -
1 stop12h 26m
Deal found 7/30![Frontier logo]()
$290
This Priceline deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am -
1 stop11h 03m
Mon 8/2412:27 pm -
1 stop11h 41m
Deal found 8/3![Frontier logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/268:05 am -
2 stops13h 07m
Sat 8/2912:27 pm -
1 stop11h 41m
Deal found 7/30![Multiple Airlines logo]()
$294
Best flights from Chicago to SpringfieldDiscover carefully curated flight deals from Chicago to Springfield that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
Discover carefully curated flight deals from Chicago to Springfield that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:45 pm -
1 stop3h 40m
Sat 9/127:55 am -
Nonstop2h 20m
Deal found 7/30![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 7/30. 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 8/266:42 pm -
1 stop4h 09m
Sat 8/291:09 pm -
1 stop6h 24m
Deal found 7/30![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:25 pm -
Nonstop2h 20m
Sat 9/1911:45 am -
Nonstop2h 45m
Deal found 8/1![United Airlines logo]()
$315
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:20 pm -
1 stop7h 39m
Mon 11/307:50 am -
1 stop7h 40m
Deal found 8/4![JetBlue logo]()
$371
This Delta deal was found by Cheapflights users on 7/30. 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 8/226:42 pm -
1 stop4h 09m
Thu 8/277:00 am -
1 stop5h 51m
Deal found 7/30![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 7/30. 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 8/259:25 am -
1 stop4h 25m
Sat 8/298:25 am -
2 stops9h 40m
Deal found 7/30![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:06 am -
Nonstop2h 23m
Mon 8/316:00 am -
Nonstop2h 46m
Deal found 8/4![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 7/30. 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 8/246:42 pm -
1 stop4h 09m
Wed 8/266:00 am -
1 stop6h 51m
Deal found 7/30![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Tue 8/2511:06 am -
Nonstop2h 23m
Mon 8/314:50 pm -
Nonstop2h 45m
Deal found 7/31![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 7/31. 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 8/251:00 pm -
Nonstop2h 05m
Tue 9/17:45 am -
Nonstop2h 20m
Deal found 7/31![Southwest logo]()
$315
This JetBlue deal was found by Cheapflights users on 8/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:35 pm -
1 stop8h 20m
Sun 10/116:25 am -
1 stop6h 22m
Deal found 8/1![JetBlue logo]()
$375
This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:45 pm -
1 stop5h 06m
Mon 9/712:55 pm -
1 stop6h 38m
Deal found 8/1![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 8/1. 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 9/151:00 pm -
Nonstop2h 05m
Tue 9/223:30 pm -
1 stop6h 35m
Deal found 8/1![Southwest logo]()
$325
This United Airlines deal was found by Cheapflights users on 7/31. 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 12/246:07 pm -
1 stop4h 54m
Wed 12/307:45 pm -
1 stop4h 37m
Deal found 7/31![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 7/31. 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 8/259:25 am -
1 stop6h 45m
Mon 8/316:20 pm -
Nonstop2h 20m
Deal found 7/31![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:45 am -
Nonstop2h 15m
Sat 8/298:25 am -
2 stops5h 40m
Deal found 8/4![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:15 pm -
Nonstop2h 23m
Wed 9/169:15 am -
Nonstop2h 46m
Deal found 8/3![United Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:45 am -
1 stop4h 20m
Sun 9/611:44 am -
Nonstop2h 45m
Deal found 8/1![United Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:06 am -
Nonstop2h 23m
Wed 9/96:00 am -
Nonstop2h 46m
Deal found 8/4![United Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:30 pm -
Nonstop2h 23m
Sun 10/116:00 am -
1 stop4h 38m
Deal found 8/1![United Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:30 am -
Nonstop2h 19m
Sun 10/186:05 am -
Nonstop2h 45m
Deal found 8/1![United Airlines logo]()
$477
Last-minute flights from Chicago to SpringfieldDiscover last-minute flight deals from Chicago to Springfield. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Springfield. Data last updated August 4, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 7/30. 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 8/135:27 pm -
1 stop5h 53m
Mon 8/175:07 pm -
1 stop7h 37m
Deal found 7/30![JetBlue logo]()
$285
This JetBlue deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:27 pm -
1 stop5h 53m
Fri 8/215:07 pm -
1 stop7h 37m
Deal found 8/3![JetBlue logo]()
$295
This CheapOair deal was found by Cheapflights users on 7/30. 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.
Wed 8/196:30 pm -
1 stop4h 50m
Wed 8/2612:27 pm -
1 stop11h 41m
Deal found 7/30![Multiple Airlines logo]()
$282
This Priceline deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am -
1 stop11h 03m
Mon 8/2412:27 pm -
1 stop11h 41m
Deal found 8/3![Frontier logo]()
$292
This United Airlines deal was found by Cheapflights users on 7/30. 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 8/247:15 am -
Nonstop2h 23m
Mon 8/314:50 pm -
Nonstop2h 45m
Deal found 7/30![United Airlines logo]()
$277
This JetBlue deal was found by Cheapflights users on 7/30. 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 8/245:27 pm -
1 stop5h 53m
Thu 8/275:07 pm -
1 stop7h 37m
Deal found 7/30![JetBlue logo]()
$289
This Southwest deal was found by Cheapflights users on 7/30. 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 8/251:00 pm -
Nonstop2h 05m
Sat 8/293:50 pm -
Nonstop2h 25m
Deal found 7/30![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/268:05 am -
2 stops13h 07m
Sat 8/2912:27 pm -
1 stop11h 41m
Deal found 7/30![Multiple Airlines logo]()
$294
This Priceline deal was found by Cheapflights users on 8/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am -
1 stop11h 03m
Tue 9/11:42 pm -
1 stop10h 45m
Deal found 8/1![Frontier logo]()
$288
This CheapOair deal was found by Cheapflights users on 7/31. 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 9/37:44 pm -
1 stop14h 48m
Mon 9/712:27 pm -
1 stop11h 41m
Deal found 7/31![Frontier logo]()
$280
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:56 am -
Nonstop2h 26m
Sun 9/67:00 am -
Nonstop2h 53m
Deal found 8/1![American Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:00 pm -
Nonstop2h 20m
Mon 9/76:00 am -
Nonstop2h 46m
Deal found 8/3![United Airlines logo]()
$296
One-way flights from Chicago to SpringfieldSearch for one-way flight options from Chicago to Springfield. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
Search for one-way flight options from Chicago to Springfield. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 11/27:50 am -
2 stops30h 11m
Deal found 8/2![Multiple Airlines logo]()
$147
This JetBlue deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:27 pm -
1 stop5h 53m
Deal found 8/3![JetBlue logo]()
$148
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:30 am -
1 stop5h 11m
Deal found 8/4![Delta logo]()
$149
This Southwest deal was found by Cheapflights users on 7/30. 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 10/3011:00 am -
1 stop5h 15m
Deal found 7/30![Southwest logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Thu 9/107:28 pm -
2 stops27h 16m
Deal found 8/2![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:05 am -
2 stops31h 25m
Deal found 7/31![Multiple Airlines logo]()
$151
This Frontier deal was found by Cheapflights users on 8/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/29:26 am -
1 stop9h 35m
Deal found 8/2![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:10 pm -
2 stops19h 17m
Deal found 8/1![Multiple Airlines logo]()
$153
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:50 pm -
2 stops7h 25m
Deal found 7/30![Southwest logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:56 pm -
2 stops24h 22m
Deal found 7/31![Frontier logo]()
$157
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/313:00 pm -
Nonstop2h 20m
Deal found 8/1![United Airlines logo]()
$158
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:00 pm -
Nonstop2h 05m
Deal found 8/3![Southwest logo]()
$158
Find flight deals from Chicago to Springfield
Keep the following information in mind while searching for Chicago to Springfield flight deals. Data was last updated August 4, 2026.
Round-trip from | $277 (United Airlines) |
|---|---|
One-way from | $147 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $318 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Springfield that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 4, 2026.
Use the filters below to find and compare flights from Chicago to Springfield that are best for you.
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Cheapest round-trip
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Wed 9/9
12:45 pm-5:25 pm
1 stop3h 40m
Hartford Bradley Intl
Sat 9/12
7:55 am-9:15 am
Nonstop2h 20m
$287
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Wed 8/26
6:42 pm-11:51 pm
1 stop4h 09m
Hartford Bradley Intl
Sat 8/29
1:09 pm-6:33 pm
1 stop6h 24m
$297
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Sat 8/22
6:42 pm-11:51 pm
1 stop4h 09m
Hartford Bradley Intl
Thu 8/27
7:00 am-11:51 am
1 stop5h 51m
$297
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Mon 8/24
6:42 pm-11:51 pm
1 stop4h 09m
Hartford Bradley Intl
Wed 8/26
6:00 am-11:51 am
1 stop6h 51m
$297
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Tue 8/25
9:25 am-2:50 pm
1 stop4h 25m
Hartford Bradley Intl
Sat 8/29
8:25 am-5:05 pm
2 stops9h 40m
$302
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Wed 9/16
2:25 pm-5:45 pm
Nonstop2h 20m
Hartford Bradley Intl
Sat 9/19
11:45 am-1:30 pm
Nonstop2h 45m
$315
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Wed 8/26
11:06 am-2:29 pm
Nonstop2h 23m
Hartford Bradley Intl
Mon 8/31
6:00 am-7:46 am
Nonstop2h 46m
$315
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Tue 8/25
11:06 am-2:29 pm
Nonstop2h 23m
Hartford Bradley Intl
Mon 8/31
4:50 pm-6:35 pm
Nonstop2h 45m
$315
Quickest round-trip
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Tue 8/25
1:00 pm-4:05 pm
Nonstop2h 05m
Hartford Bradley Intl
Tue 9/1
7:45 am-9:05 am
Nonstop2h 20m
$315
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Sat 9/5
5:45 pm-11:51 pm
1 stop5h 06m
Hartford Bradley Intl
Mon 9/7
12:55 pm-6:33 pm
1 stop6h 38m
$316
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Chicago to Springfield
Have a flexible travel schedule? Discover the best time to fly to Springfield from Chicago with our price prediction graph.
ORD-BDL
MDW-BDL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Springfield
CHI-SFY
ORD-BDL
MDW-BDL
How much does it cost to fly round-trip from Chicago to Springfield?
Airfare is typical for this route at the moment.
Chicago to Springfield flights typically cost between $242 and $433 in August.The cheapest round-trip price found within the last 5 days was $277 on United Airlines (Aug 25-Aug 29).
Reviews of airlines servicing Springfield
Get insights into the airlines that provide service to Springfield. 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 Springfield. Reviews last updated August 4, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to Springfield. 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
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Springfield. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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