$141+ Cheap flights from Springfield, MA, MA to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/31. 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 Springfield to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Springfield to Chicago are usually found in January or October, booked 57 days in advance, depart on a Wednesday or Saturday and return on a Thursday
Cheap flight deals from Springfield to Chicago
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Best
Last-minute
One-way
Cheapest flights from Springfield to ChicagoExplore the most affordable flight options available from Springfield to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 9, 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 May 9, 2026.
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 6/312:12 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Tue 6/236:00 am
ORD
- BDL
1 stop7h 06m
United Airlines
Deal found 5/4![United Airlines logo]()
$343
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:00 am
BDL
- MDW
Nonstop2h 25m
Southwest
Tue 6/212:55 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 5/4![Southwest logo]()
$344
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 6/38:47 am
BDL
- ORD
Nonstop2h 53m
United Airlines
Thu 6/46:25 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 5/4![United Airlines logo]()
$344
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.
Fri 5/227:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Sun 5/243:27 pm
ORD
- BDL
1 stop7h 28m
JetBlue
Deal found 5/4![JetBlue logo]()
$345
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 7/1012:24 pm
BDL
- RFD
1 stop21h 51m
Multiple Airlines
Mon 7/137:50 pm
RFD
- BDL
1 stop27h 51m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$347
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:50 am
BDL
- MDW
Nonstop2h 25m
Southwest
Tue 6/98:40 am
MDW
- BDL
2 stops8h 10m
Southwest
Deal found 5/4![Southwest logo]()
$348
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.
Thu 5/287:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Mon 6/16:15 am
ORD
- BDL
1 stop16h 40m
JetBlue
Deal found 5/6![JetBlue logo]()
$349
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:25 am
BDL
- ORD
1 stop8h 20m
JetBlue
Sun 5/243:27 pm
ORD
- BDL
1 stop7h 28m
JetBlue
Deal found 5/7![JetBlue logo]()
$350
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 5/295:40 pm
BDL
- RFD
1 stop16h 41m
Multiple Airlines
Mon 6/18:35 am
RFD
- BDL
2 stops31h 35m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$352
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:10 am
BDL
- ORD
Nonstop2h 50m
American Airlines
Thu 6/257:26 pm
ORD
- BDL
Nonstop2h 20m
American Airlines
Deal found 5/8![American Airlines logo]()
$352
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 6/212:25 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Wed 6/177:50 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 5/7![Southwest logo]()
$353
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 6/37:45 pm
BDL
- ORD
1 stop4h 41m
United Airlines
Wed 6/106:30 am
ORD
- BDL
1 stop6h 36m
United Airlines
Deal found 5/4![United Airlines logo]()
$353
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 May 9, 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 May 9, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:40 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Wed 6/107:50 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 5/4![Southwest logo]()
$344
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 7/1012:24 pm
BDL
- RFD
1 stop21h 51m
Multiple Airlines
Mon 7/137:50 pm
RFD
- BDL
1 stop27h 51m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$347
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.
Tue 6/164:55 pm
BDL
- ORD
Nonstop2h 49m
United Airlines
Tue 6/306:30 am
ORD
- BDL
1 stop6h 36m
United Airlines
Deal found 5/7![United Airlines logo]()
$363
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.
Fri 6/197:10 pm
BDL
- ORD
1 stop5h 49m
Delta
Wed 6/249:48 am
ORD
- BDL
1 stop7h 16m
Delta
Deal found 5/4![Delta 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.
Sun 8/911:04 am
BDL
- ORD
1 stop7h 20m
Sun Country Air
Thu 8/136:31 pm
ORD
- BDL
1 stop15h 16m
Sun Country Air
Deal found 5/8![Sun Country Air logo]()
$465
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1212:38 pm
BDL
- RFD
1 stop21h 39m
Multiple Airlines
Mon 6/157:53 pm
RFD
- BDL
1 stop27h 48m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$362
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.
Thu 6/46:00 am
BDL
- ORD
1 stop6h 53m
United Airlines
Mon 6/86:26 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 5/6![United Airlines logo]()
$365
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.
Thu 6/47:10 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Mon 6/82:45 pm
MDW
- BDL
2 stops8h 30m
Southwest
Deal found 5/6![Southwest logo]()
$370
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.
Wed 9/3012:45 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Sat 10/36:30 am
MDW
- BDL
2 stops7h 25m
Southwest
Deal found 5/8![Southwest logo]()
$370
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 5/268:10 am
BDL
- RFD
2 stops26h 11m
Multiple Airlines
Fri 5/298:03 pm
RFD
- BDL
1 stop21h 55m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$400
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 7/153:02 pm
BDL
- ORD
1 stop7h 30m
United Airlines
Sun 7/197:00 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Deal found 5/8![United Airlines logo]()
$403
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.
Sat 5/304:55 pm
BDL
- MDW
1 stop4h 45m
Southwest
Wed 6/39:50 am
MDW
- BDL
2 stops8h 10m
Southwest
Deal found 5/8![Southwest logo]()
$379
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 7/296:00 am
BDL
- ORD
1 stop4h 36m
United Airlines
Sat 8/16:30 am
ORD
- BDL
1 stop6h 36m
United Airlines
Deal found 5/8![United Airlines logo]()
$413
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.
Tue 8/43:05 pm
BDL
- MDW
2 stops8h 15m
Southwest
Tue 8/187:40 am
MDW
- BDL
2 stops8h 30m
Southwest
Deal found 5/5![Southwest logo]()
$383
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2912:29 pm
BDL
- RFD
2 stops23h 08m
Multiple Airlines
Sat 8/19:05 am
RFD
- BDL
1 stop11h 48m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$432
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.
Fri 5/297:20 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Mon 6/13:50 pm
MDW
- BDL
2 stops6h 20m
Southwest
Deal found 5/5![Southwest logo]()
$384
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.
Fri 6/196:09 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Mon 6/227:15 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Deal found 5/8![United Airlines logo]()
$433
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.
Fri 6/2612:38 pm
BDL
- RFD
1 stop21h 39m
Multiple Airlines
Sat 7/49:05 am
RFD
- BDL
1 stop11h 48m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$439
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.
Fri 6/194:55 pm
BDL
- ORD
Nonstop2h 49m
United Airlines
Sun 6/217:15 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Deal found 5/8![United Airlines logo]()
$433
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 6/47:10 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Sun 6/77:40 am
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 5/5![Southwest logo]()
$394
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.
Sat 7/46:15 am
BDL
- RFD
2 stops29h 22m
Multiple Airlines
Wed 7/811:19 am
RFD
- BDL
1 stop11h 52m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$452
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.
Thu 7/303:02 pm
BDL
- ORD
1 stop7h 30m
United Airlines
Fri 7/312:30 pm
ORD
- BDL
Nonstop2h 37m
United Airlines
Deal found 5/4![United Airlines logo]()
$443
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.
Wed 6/172:35 pm
BDL
- MDW
1 stop4h 20m
Southwest
Thu 6/187:45 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 5/8![Southwest logo]()
$403
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.
Sat 6/1312:29 pm
BDL
- RFD
2 stops23h 08m
Multiple Airlines
Wed 6/1711:21 am
RFD
- BDL
1 stop11h 50m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$458
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.
Tue 10/66:00 pm
BDL
- MDW
1 stop4h 50m
Southwest
Fri 10/167:50 am
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 5/6![Southwest logo]()
$403
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 6/41:54 pm
BDL
- RFD
2 stops18h 51m
Multiple Airlines
Mon 6/87:53 pm
RFD
- BDL
1 stop27h 48m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$469
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.
Sun 9/276:15 am
BDL
- ORD
Nonstop2h 35m
United Airlines
Wed 9/306:20 pm
ORD
- BDL
Nonstop2h 02m
United Airlines
Deal found 5/8![United Airlines logo]()
$473
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 6/1612:40 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Sat 6/276:30 am
MDW
- BDL
1 stop7h 30m
Southwest
Deal found 5/8![Southwest logo]()
$403
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2412:40 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Wed 7/297:50 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 5/4![Southwest logo]()
$408
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:57 pm
BDL
- RFD
2 stops15h 20m
Multiple Airlines
Mon 6/297:48 pm
RFD
- BDL
1 stop27h 53m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$510
Last-minute flights from Springfield to ChicagoDiscover last-minute flight deals from Springfield to Chicago. Data last updated May 9, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Chicago. Data last updated May 9, 2026 and is based on user searches.
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:25 am
BDL
- ORD
1 stop8h 20m
JetBlue
Sun 5/243:27 pm
ORD
- BDL
1 stop7h 28m
JetBlue
Deal found 5/7![JetBlue logo]()
$350
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:48 pm
BDL
- ORD
1 stop10h 38m
Frontier
Fri 5/2912:33 am
ORD
- BDL
1 stop11h 11m
Frontier
Deal found 5/4![Frontier logo]()
$345
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.
Thu 5/287:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Mon 6/16:15 am
ORD
- BDL
1 stop16h 40m
JetBlue
Deal found 5/6![JetBlue logo]()
$349
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 5/295:40 pm
BDL
- RFD
1 stop16h 41m
Multiple Airlines
Mon 6/18:35 am
RFD
- BDL
2 stops31h 35m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$352
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:00 am
BDL
- MDW
Nonstop2h 25m
Southwest
Tue 6/212:55 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 5/4![Southwest logo]()
$344
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.
Sat 5/307:00 am
BDL
- MDW
Nonstop2h 25m
Southwest
Wed 6/37:40 am
MDW
- BDL
Nonstop2h 00m
Southwest
Deal found 5/8![Southwest logo]()
$354
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:50 am
BDL
- MDW
Nonstop2h 25m
Southwest
Tue 6/98:40 am
MDW
- BDL
2 stops8h 10m
Southwest
Deal found 5/4![Southwest logo]()
$348
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 6/312:12 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Tue 6/236:00 am
ORD
- BDL
1 stop7h 06m
United Airlines
Deal found 5/4![United Airlines logo]()
$343
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 6/38:47 am
BDL
- ORD
Nonstop2h 53m
United Airlines
Thu 6/46:25 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 5/4![United Airlines logo]()
$344
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.
Wed 6/312:25 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Wed 6/177:50 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 5/7![Southwest logo]()
$353
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 6/37:45 pm
BDL
- ORD
1 stop4h 41m
United Airlines
Wed 6/106:30 am
ORD
- BDL
1 stop6h 36m
United Airlines
Deal found 5/4![United Airlines logo]()
$353
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:10 am
BDL
- ORD
Nonstop2h 50m
American Airlines
Thu 6/257:26 pm
ORD
- BDL
Nonstop2h 20m
American Airlines
Deal found 5/8![American Airlines logo]()
$352
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 May 9, 2026.
Search for one-way flight options from Springfield to Chicago. Find affordable one-way fares based on user searches. Data last updated May 9, 2026.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3112:24 pm
BDL
- ORD
1 stop11h 41m
Frontier
Deal found 5/4![Frontier logo]()
$141
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.
Thu 5/288:00 am
BDL
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$142
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.
Mon 5/256:57 pm
BDL
- MDW
3 stops28h 05m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$144
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.
Mon 5/256:57 pm
BDL
- ORD
3 stops25h 44m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$144
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.
Sun 5/317:10 am
BDL
- MDW
2 stops28h 59m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$146
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.
Sun 5/317:10 am
BDL
- ORD
2 stops25h 45m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$146
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.
Mon 6/296:00 am
BDL
- MDW
2 stops30h 12m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$148
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.
Sun 5/246:20 am
BDL
- ORD
2 stops50h 35m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$148
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:35 am
BDL
- MDW
2 stops15h 33m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$149
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 6/48:00 am
BDL
- MDW
2 stops15h 02m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$151
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.
Sun 6/77:00 am
BDL
- ORD
2 stops25h 55m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$151
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.
Mon 7/136:00 am
BDL
- ORD
2 stops26h 53m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$152
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 May 9, 2026.
Round-trip from | $344 (Southwest) |
|---|---|
One-way from | $141 (Frontier) |
Popular in | April |
Cheapest in | January |
Average price | $410 |
Cheapflights Fare Finder
Customize your flight search to find flights from Springfield to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 9, 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
Quickest round-trip
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Mon 6/8
12:40 pm-2:05 pm
Nonstop2h 25m
Chicago Midway
Wed 6/10
7:50 am-11:00 am
Nonstop2h 10m
$344
HartfordChicago
BDL - RFD
BDLRFD
Hartford Bradley Intl
Fri 7/10
12:24 pm-9:15 am
1 stop21h 51m
Chicago Greater Rockford
Mon 7/13
7:50 pm-12:41 am
1 stop27h 51m
$347
HartfordChicago
BDL - RFD
BDLRFD
Hartford Bradley Intl
Fri 6/12
12:38 pm-9:17 am
1 stop21h 39m
Chicago Greater Rockford
Mon 6/15
7:53 pm-12:41 am
1 stop27h 48m
$362
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Tue 6/16
4:55 pm-6:44 pm
Nonstop2h 49m
Chicago O'Hare Intl
Tue 6/30
6:30 am-2:06 pm
1 stop6h 36m
$363
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Thu 6/4
6:00 am-11:53 am
1 stop6h 53m
Chicago O'Hare Intl
Mon 6/8
6:26 pm-9:49 pm
Nonstop2h 23m
$365
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Thu 6/4
7:10 pm-8:40 pm
Nonstop2h 30m
Chicago Midway
Mon 6/8
2:45 pm-12:15 am
2 stops8h 30m
$370
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Wed 9/30
12:45 pm-2:05 pm
Nonstop2h 20m
Chicago Midway
Sat 10/3
6:30 am-2:55 pm
2 stops7h 25m
$370
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sat 5/30
4:55 pm-8:40 pm
1 stop4h 45m
Chicago Midway
Wed 6/3
9:50 am-7:00 pm
2 stops8h 10m
$379
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Tue 8/4
3:05 pm-10:20 pm
2 stops8h 15m
Chicago Midway
Tue 8/18
7:40 am-5:10 pm
2 stops8h 30m
$383
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Fri 5/29
7:20 pm-8:45 pm
Nonstop2h 25m
Chicago Midway
Mon 6/1
3:50 pm-11:10 pm
2 stops6h 20m
$384
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Springfield to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Springfield with our price prediction graph.
BDL-ORD
BDL-RFD
BDL-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Springfield to Chicago
SFY-CHI
BDL-ORD
BDL-RFD
BDL-MDW
How much does it cost to fly round-trip from Springfield to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 9, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue 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
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
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 Springfield to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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