$128+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI
Jun 8 — Jun 151
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 August or September, booked 69 days in advance, depart on a Thursday or Saturday and return on a Wednesday
Cheap flight deals from Chicago to Springfield
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Best
Last-minute
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 May 9, 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 May 9, 2026.
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:13 pm
ORD
- BDL
1 stop17h 16m
Multiple Airlines
Sun 7/196:45 am
BDL
- ORD
1 stop16h 10m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$303
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:22 pm
ORD
- BDL
1 stop5h 37m
JetBlue
Sun 6/146:45 am
BDL
- ORD
1 stop27h 00m
JetBlue
Deal found 5/5![JetBlue logo]()
$304
This CheapOair deal was found by Cheapflights users on 5/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:11 pm
ORD
- BDL
1 stop7h 44m
JetBlue
Mon 5/257:15 am
BDL
- ORD
1 stop27h 39m
JetBlue
Deal found 5/4![JetBlue logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- BDL
1 stop30h 52m
Multiple Airlines
Tue 6/237:15 am
BDL
- ORD
2 stops13h 35m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$315
This CheapOair deal was found by Cheapflights users on 5/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:11 pm
ORD
- BDL
1 stop22h 34m
Multiple Airlines
Sun 6/77:15 am
BDL
- ORD
1 stop27h 39m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$318
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/263:27 pm
ORD
- BDL
1 stop7h 28m
JetBlue
Thu 5/287:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Deal found 5/5![JetBlue logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- BDL
1 stop18h 10m
Multiple Airlines
Wed 6/247:35 am
BDL
- ORD
2 stops13h 15m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$321
This CheapOair deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:39 pm
ORD
- BDL
1 stop7h 13m
JetBlue
Tue 6/166:45 am
BDL
- ORD
1 stop15h 45m
JetBlue
Deal found 5/6![JetBlue logo]()
$323
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:11 pm
ORD
- BDL
1 stop24h 47m
Multiple Airlines
Mon 6/17:15 am
BDL
- ORD
2 stops25h 45m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$324
This JetBlue deal was found by Cheapflights users on 5/4. 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.
Thu 5/213:40 pm
ORD
- BDL
1 stop7h 15m
JetBlue
Sat 5/237:15 am
BDL
- ORD
1 stop8h 01m
JetBlue
Deal found 5/4![JetBlue logo]()
$325
This Expedia deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Mon 7/136:45 am
BDL
- ORD
2 stops13h 40m
JetBlue
Deal found 5/7![JetBlue logo]()
$330
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:50 am
MDW
- BDL
Nonstop2h 10m
Southwest
Tue 8/412:45 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Deal found 5/6![Southwest logo]()
$353
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 May 9, 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 May 9, 2026.
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:45 am
MDW
- BDL
Nonstop2h 10m
Southwest
Tue 6/98:55 am
BDL
- MDW
1 stop6h 05m
Southwest
Deal found 5/5![Southwest logo]()
$364
This Delta deal was found by Cheapflights users on 5/4. 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.
Thu 6/410:59 am
MDW
- BDL
1 stop6h 11m
Delta
Tue 6/911:41 am
BDL
- MDW
1 stop5h 35m
Delta
Deal found 5/4![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:10 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Sat 7/113:02 pm
BDL
- ORD
1 stop4h 48m
United Airlines
Deal found 5/6![United Airlines logo]()
$403
This Sun Country Air deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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.
Thu 6/118:19 pm
ORD
- BDL
1 stop13h 18m
Sun Country Air
Fri 6/2611:18 am
BDL
- ORD
1 stop7h 06m
Sun Country Air
Deal found 5/8![Sun Country Air logo]()
$465
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:40 am
MDW
- BDL
Nonstop2h 00m
Southwest
Mon 6/14:40 pm
BDL
- MDW
1 stop6h 40m
Southwest
Deal found 5/7![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 5/4. 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.
Mon 8/106:40 am
ORD
- BDL
1 stop5h 08m
Delta
Tue 8/187:00 am
BDL
- ORD
1 stop6h 36m
Delta
Deal found 5/4![Delta logo]()
$403
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:00 pm
ORD
- BDL
1 stop6h 57m
United Airlines
Sun 9/1310:00 am
BDL
- ORD
Nonstop2h 44m
United Airlines
Deal found 5/7![United Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
Mon 6/15:20 am
BDL
- ORD
1 stop10h 00m
Southwest
Deal found 5/7![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Wed 8/125:25 am
BDL
- MDW
1 stop4h 52m
Delta
Deal found 5/5![Delta logo]()
$413
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 8/186:45 am
ORD
- BDL
Nonstop2h 14m
United Airlines
Wed 8/1910:33 am
BDL
- ORD
1 stop7h 27m
United Airlines
Deal found 5/4![United Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
Mon 6/15:50 am
BDL
- ORD
2 stops9h 30m
Southwest
Deal found 5/6![Southwest logo]()
$399
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Fri 8/145:25 am
BDL
- MDW
1 stop4h 52m
Delta
Deal found 5/5![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:50 pm
MDW
- BDL
2 stops6h 20m
Southwest
Mon 6/12:05 pm
BDL
- MDW
2 stops7h 00m
Southwest
Deal found 5/6![Southwest logo]()
$399
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:30 am
ORD
- BDL
1 stop6h 36m
United Airlines
Sun 8/98:47 am
BDL
- ORD
Nonstop2h 53m
United Airlines
Deal found 5/6![United Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:58 pm
MDW
- BDL
1 stop3h 37m
Delta
Mon 6/156:00 am
BDL
- MDW
1 stop5h 09m
Delta
Deal found 5/7![Delta logo]()
$423
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 7/77:50 am
MDW
- BDL
2 stops5h 10m
Southwest
Thu 7/97:10 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Deal found 5/8![Southwest logo]()
$408
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/2711:03 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Sat 5/3012:12 pm
BDL
- ORD
Nonstop2h 53m
United Airlines
Deal found 5/8![United Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:58 pm
MDW
- BDL
1 stop3h 37m
Delta
Mon 6/156:00 am
BDL
- MDW
1 stop5h 09m
Delta
Deal found 5/7![Delta logo]()
$423
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:45 pm
MDW
- BDL
Nonstop2h 00m
Southwest
Fri 6/55:50 am
BDL
- MDW
2 stops8h 55m
Southwest
Deal found 5/5![Southwest logo]()
$409
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:22 pm
ORD
- BDL
1 stop5h 13m
Delta
Sun 6/211:15 pm
BDL
- ORD
1 stop6h 14m
Delta
Deal found 5/6![Delta logo]()
$431
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:40 am
MDW
- BDL
2 stops8h 10m
Southwest
Fri 6/122:50 pm
BDL
- MDW
2 stops6h 30m
Southwest
Deal found 5/7![Southwest logo]()
$423
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:18 pm
ORD
- BDL
1 stop4h 56m
Delta
Thu 8/136:50 am
BDL
- ORD
1 stop5h 47m
Delta
Deal found 5/4![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/193:55 pm
ORD
- BDL
1 stop6h 48m
Delta
Sun 6/211:15 pm
BDL
- ORD
1 stop6h 14m
Delta
Deal found 5/8![Delta logo]()
$471
Last-minute flights from Chicago to SpringfieldDiscover last-minute flight deals from Chicago to Springfield. Data last updated May 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Springfield. Data last updated May 9, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/263:27 pm
ORD
- BDL
1 stop7h 28m
JetBlue
Thu 5/287:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Deal found 5/5![JetBlue logo]()
$319
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Mon 6/17:20 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Deal found 5/7![Southwest logo]()
$355
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:11 pm
ORD
- BDL
1 stop24h 47m
Multiple Airlines
Mon 6/17:15 am
BDL
- ORD
2 stops25h 45m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:45 pm
MDW
- BDL
Nonstop2h 00m
Southwest
Tue 6/96:30 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Deal found 5/5![Southwest logo]()
$354
This Mytrip deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:11 pm
ORD
- BDL
1 stop22h 34m
Multiple Airlines
Mon 6/811:56 am
BDL
- ORD
1 stop7h 13m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$330
This CheapOair deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:39 pm
ORD
- BDL
1 stop7h 13m
JetBlue
Tue 6/166:45 am
BDL
- ORD
1 stop15h 45m
JetBlue
Deal found 5/6![JetBlue logo]()
$323
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:22 pm
ORD
- BDL
1 stop5h 37m
JetBlue
Sun 6/146:45 am
BDL
- ORD
1 stop27h 00m
JetBlue
Deal found 5/5![JetBlue logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- BDL
1 stop30h 52m
Multiple Airlines
Tue 6/237:15 am
BDL
- ORD
2 stops13h 35m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$315
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- BDL
1 stop18h 10m
Multiple Airlines
Sun 6/216:45 am
BDL
- ORD
1 stop27h 00m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- BDL
1 stop18h 10m
Multiple Airlines
Wed 6/247:35 am
BDL
- ORD
2 stops13h 15m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:26 pm
ORD
- BDL
Nonstop2h 20m
American Airlines
Wed 6/247:10 am
BDL
- ORD
Nonstop2h 50m
American Airlines
Deal found 5/4![American Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 5/4. 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 6/173:53 pm
ORD
- BDL
1 stop7h 06m
United Airlines
Wed 6/248:47 am
BDL
- ORD
Nonstop2h 53m
United Airlines
Deal found 5/4![United Airlines logo]()
$343
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 May 9, 2026.
Search for one-way flight options from Chicago to Springfield. Find affordable one-way fares based on user searches. Data last updated May 9, 2026.
This Super.com deal was found by Cheapflights users on 5/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/243:27 pm
ORD
- BDL
1 stop7h 28m
JetBlue
Deal found 5/4![JetBlue logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:55 am
ORD
- BDL
2 stops40h 04m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:27 pm
MDW
- BDL
2 stops22h 27m
Frontier
Deal found 5/4![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:11 pm
ORD
- BDL
1 stop22h 34m
Frontier
Deal found 5/5![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
MDW
- BDL
2 stops15h 43m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$131
This JetBlue deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/53:27 pm
ORD
- BDL
1 stop7h 25m
JetBlue
Deal found 5/6![JetBlue logo]()
$133
This Expedia deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:22 pm
ORD
- BDL
1 stop5h 37m
JetBlue
Deal found 5/5![JetBlue logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:50 pm
ORD
- BDL
2 stops33h 09m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:04 pm
MDW
- BDL
2 stops34h 55m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:52 am
ORD
- BDL
2 stops13h 20m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$139
This Booking.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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.
Tue 6/234:59 pm
ORD
- BDL
1 stop18h 10m
Frontier
Deal found 5/8![Frontier logo]()
$141
This CheapOair deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/45:11 pm
ORD
- BDL
1 stop22h 34m
Frontier
Deal found 5/9![Frontier logo]()
$146
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 May 9, 2026.
Round-trip from | $303 (CheapOair) |
|---|---|
One-way from | $128 (Super.com) |
Popular in | April |
Cheapest in | August |
Average price | $375 |
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 May 9, 2026.
Use the filters below to find and compare flights from Chicago to Springfield that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Thu 6/4
7:45 am-10:55 am
Nonstop2h 10m
Hartford Bradley Intl
Tue 6/9
8:55 am-2:00 pm
1 stop6h 05m
$364
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Thu 6/4
10:59 am-6:10 pm
1 stop6h 11m
Hartford Bradley Intl
Tue 6/9
11:41 am-4:16 pm
1 stop5h 35m
$364
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Thu 5/28
7:40 am-10:40 am
Nonstop2h 00m
Hartford Bradley Intl
Mon 6/1
4:40 pm-10:20 pm
1 stop6h 40m
$365
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Thu 5/28
2:40 pm-11:10 pm
2 stops7h 30m
Hartford Bradley Intl
Mon 6/1
5:20 am-2:20 pm
1 stop10h 00m
$380
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Fri 5/29
2:40 pm-11:10 pm
2 stops7h 30m
Hartford Bradley Intl
Mon 6/1
5:50 am-2:20 pm
2 stops9h 30m
$399
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Fri 5/29
3:50 pm-11:10 pm
2 stops6h 20m
Hartford Bradley Intl
Mon 6/1
2:05 pm-8:05 pm
2 stops7h 00m
$399
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Wed 7/8
6:10 pm-9:33 pm
Nonstop2h 23m
Hartford Bradley Intl
Sat 7/11
3:02 pm-6:50 pm
1 stop4h 48m
$403
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Mon 8/10
6:40 am-12:48 pm
1 stop5h 08m
Hartford Bradley Intl
Tue 8/18
7:00 am-12:36 pm
1 stop6h 36m
$403
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Tue 7/7
7:50 am-2:00 pm
2 stops5h 10m
Hartford Bradley Intl
Thu 7/9
7:10 pm-8:40 pm
Nonstop2h 30m
$408
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Thu 9/10
4:00 pm-11:57 pm
1 stop6h 57m
Hartford Bradley Intl
Sun 9/13
10:00 am-11:44 am
Nonstop2h 44m
$409
Showing 1-10 of 44 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?
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 May 9, 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.
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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