$60+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Mar 4 — Mar 111
1 adult, Economy
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Find cheap flights from Springfield to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Springfield to Chicago are usually found in October or September, booked 66 days in advance, depart on a Wednesday or Thursday 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 February 2, 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 February 2, 2026.
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:52 am
BDL
- MDW
1 stop10h 35m
Frontier
Thu 2/266:25 am
MDW
- BDL
1 stop6h 07m
Frontier
Deal found 2/1![Frontier logo]()
$244
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/58:31 pm
BDL
- ORD
1 stop15h 04m
Frontier
Mon 2/911:51 am
ORD
- BDL
1 stop22h 33m
Frontier
Deal found 2/1![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 1/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:07 pm
BDL
- MDW
1 stop10h 12m
Frontier
Sun 5/39:14 am
MDW
- BDL
1 stop9h 03m
Frontier
Deal found 1/31![Frontier logo]()
$255
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/191:07 pm
BDL
- ORD
1 stop10h 32m
Frontier
Mon 4/205:01 am
ORD
- BDL
1 stop6h 14m
Frontier
Deal found 2/1![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sun 3/81:07 pm
BDL
- MDW
1 stop7h 40m
Multiple Airlines
Mon 3/96:15 am
MDW
- BDL
2 stops16h 01m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$258
This JetBlue deal was found by Cheapflights users on 2/1. 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.
Sun 9/276:45 am
BDL
- ORD
1 stop6h 35m
JetBlue
Fri 10/21:35 pm
ORD
- BDL
1 stop7h 59m
JetBlue
Deal found 2/1![JetBlue logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Tue 3/319:10 am
BDL
- ORD
1 stop15h 28m
Multiple Airlines
Thu 4/29:06 am
ORD
- BDL
1 stop10h 20m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 2/206:17 pm
BDL
- MDW
1 stop21h 38m
Frontier
Sun 2/226:00 am
MDW
- BDL
1 stop6h 32m
Frontier
Deal found 2/1![Frontier logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/208:08 pm
BDL
- ORD
1 stop12h 51m
Multiple Airlines
Wed 4/223:49 pm
ORD
- BDL
1 stop26h 28m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/69:53 pm
BDL
- ORD
1 stop23h 10m
Multiple Airlines
Wed 4/89:06 am
ORD
- BDL
1 stop7h 33m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$267
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:07 pm
BDL
- MDW
1 stop7h 24m
Frontier
Sun 5/109:14 am
MDW
- BDL
1 stop9h 03m
Frontier
Deal found 2/1![Frontier logo]()
$270
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:07 pm
BDL
- ORD
1 stop10h 32m
Frontier
Sun 5/1010:25 am
ORD
- BDL
1 stop7h 52m
Frontier
Deal found 2/1![Frontier logo]()
$270
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 February 2, 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 February 2, 2026.
This United Airlines deal was found by Cheapflights users on 2/1. 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 7/295:04 pm
BDL
- ORD
Nonstop2h 47m
United Airlines
Sat 8/16:30 pm
ORD
- BDL
Nonstop2h 22m
United Airlines
Deal found 2/1![United Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 1/30. 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.
Fri 3/138:08 pm
BDL
- ORD
1 stop28h 30m
Multiple Airlines
Wed 3/186:10 pm
ORD
- BDL
2 stops24h 03m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 2/1. 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.
Wed 3/45:30 am
BDL
- MDW
Nonstop2h 35m
Southwest
Wed 3/117:40 am
MDW
- BDL
Nonstop2h 00m
Southwest
Deal found 2/1![Southwest logo]()
$326
This Frontier deal was found by Cheapflights users on 1/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/152:27 pm
BDL
- MDW
1 stop8h 58m
Frontier
Thu 2/197:30 am
MDW
- BDL
1 stop8h 25m
Frontier
Deal found 1/31![Frontier logo]()
$345
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Tue 6/237:00 am
BDL
- ORD
Nonstop2h 50m
American Airlines
Tue 6/301:24 pm
ORD
- BDL
Nonstop2h 21m
American Airlines
Deal found 2/1![American Airlines logo]()
$363
This Sun Country Air deal was found by Cheapflights users on 2/2. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:40 am
BDL
- ORD
1 stop6h 49m
Sun Country Air
Sun 7/126:31 pm
ORD
- BDL
1 stop14h 33m
Sun Country Air
Deal found 2/2![Sun Country Air logo]()
$375
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/144:56 pm
BDL
- ORD
1 stop8h 03m
Delta
Thu 4/167:14 am
ORD
- BDL
1 stop5h 02m
Delta
Deal found 1/31![Delta logo]()
$381
This United Airlines deal was found by Cheapflights users on 1/31. 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.
Wed 3/410:05 am
BDL
- ORD
Nonstop2h 52m
United Airlines
Wed 3/116:05 pm
ORD
- BDL
Nonstop2h 11m
United Airlines
Deal found 1/31![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 1/31. 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.
Sat 2/285:00 am
BDL
- MDW
Nonstop2h 35m
Southwest
Sun 3/19:35 am
MDW
- BDL
Nonstop2h 00m
Southwest
Deal found 1/31![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 1/31. 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.
Sat 3/217:15 am
BDL
- MDW
Nonstop2h 30m
Southwest
Tue 3/2412:55 pm
MDW
- BDL
Nonstop2h 00m
Southwest
Deal found 1/31![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 1/31. 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.
Sat 2/284:43 pm
BDL
- ORD
Nonstop2h 52m
United Airlines
Sun 3/18:50 am
ORD
- BDL
1 stop4h 14m
United Airlines
Deal found 1/31![United Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
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 2/1![Multiple Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 1/31. 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.
Sat 5/94:55 pm
BDL
- MDW
1 stop4h 45m
Southwest
Mon 5/113:50 pm
MDW
- BDL
2 stops6h 20m
Southwest
Deal found 1/31![Southwest logo]()
$353
This United Airlines deal was found by Cheapflights users on 1/30. 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 2/234:43 pm
BDL
- ORD
Nonstop2h 52m
United Airlines
Thu 2/2610:55 am
ORD
- BDL
Nonstop2h 15m
United Airlines
Deal found 1/30![United Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:25 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Sat 5/1611:25 am
MDW
- BDL
1 stop7h 40m
Southwest
Deal found 2/2![Southwest logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sun 6/71:54 pm
BDL
- RFD
2 stops18h 51m
Multiple Airlines
Wed 6/1011:21 am
RFD
- BDL
1 stop11h 50m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 1/31. 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.
Sun 3/226:00 am
BDL
- ORD
1 stop4h 49m
United Airlines
Sat 3/285:45 pm
ORD
- BDL
1 stop5h 14m
United Airlines
Deal found 1/31![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 2/1. 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.
Thu 5/1411:40 am
BDL
- MDW
Nonstop2h 25m
Southwest
Tue 5/196:00 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 2/1![Southwest logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sun 3/228:08 pm
BDL
- RFD
1 stop14h 41m
Multiple Airlines
Sat 3/281:53 pm
RFD
- BDL
1 stop15h 07m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$548
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Wed 3/183:48 pm
BDL
- RFD
1 stop26h 12m
Multiple Airlines
Sun 3/225:50 pm
RFD
- BDL
1 stop18h 21m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$724
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Thu 2/125:50 pm
BDL
- RFD
1 stop17h 11m
Multiple Airlines
Sun 2/155:53 pm
RFD
- BDL
1 stop18h 18m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$764
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Wed 3/253:48 pm
BDL
- RFD
1 stop26h 14m
Multiple Airlines
Sun 3/2912:45 pm
RFD
- BDL
1 stop16h 45m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$768
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Fri 2/207:00 am
BDL
- RFD
2 stops29h 10m
Multiple Airlines
Sun 2/225:53 pm
RFD
- BDL
1 stop18h 18m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$872
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 3/208:30 am
BDL
- RFD
2 stops11h 03m
Multiple Airlines
Sun 3/225:50 pm
RFD
- BDL
1 stop18h 21m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$908
Last-minute flights from Springfield to ChicagoDiscover last-minute flight deals from Springfield to Chicago. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Chicago. Data last updated February 2, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/58:31 pm
BDL
- ORD
1 stop15h 04m
Frontier
Mon 2/911:51 am
ORD
- BDL
1 stop22h 33m
Frontier
Deal found 2/1![Frontier logo]()
$253
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/512:11 pm
BDL
- ORD
1 stop11h 35m
Frontier
Sat 2/79:25 am
ORD
- BDL
1 stop8h 41m
Frontier
Deal found 2/1![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 1/30. 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.
Fri 2/67:00 am
BDL
- MDW
2 stops26h 43m
Multiple Airlines
Mon 2/97:00 pm
MDW
- BDL
1 stop15h 24m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sun 2/152:27 pm
BDL
- MDW
1 stop8h 58m
Frontier
Tue 2/176:00 am
MDW
- BDL
2 stops26h 23m
Frontier
Deal found 1/31![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sun 2/152:27 pm
BDL
- ORD
2 stops23h 36m
Frontier
Thu 2/195:05 am
ORD
- BDL
1 stop7h 27m
Frontier
Deal found 1/31![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Mon 2/167:05 am
BDL
- ORD
2 stops27h 17m
Multiple Airlines
Thu 2/195:05 am
ORD
- BDL
1 stop7h 27m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$276
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:27 pm
BDL
- ORD
1 stop9h 12m
Multiple Airlines
Sun 2/226:04 am
ORD
- BDL
1 stop16h 53m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 2/206:17 pm
BDL
- MDW
1 stop21h 38m
Frontier
Sun 2/226:00 am
MDW
- BDL
1 stop6h 32m
Frontier
Deal found 2/1![Frontier logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 2/206:17 pm
BDL
- ORD
1 stop22h 18m
Multiple Airlines
Mon 2/236:19 pm
ORD
- BDL
1 stop22h 52m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$270
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:52 am
BDL
- MDW
1 stop10h 35m
Frontier
Thu 2/266:25 am
MDW
- BDL
1 stop6h 07m
Frontier
Deal found 2/1![Frontier logo]()
$244
This CheapOair deal was found by Cheapflights users on 1/30. 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.
Fri 2/276:00 am
BDL
- ORD
2 stops28h 10m
Multiple Airlines
Sun 3/15:05 am
ORD
- BDL
1 stop7h 27m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:53 am
BDL
- ORD
Nonstop2h 52m
American Airlines
Sat 2/281:36 pm
ORD
- BDL
Nonstop2h 09m
American Airlines
Deal found 2/2![American Airlines logo]()
$289
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 February 2, 2026.
Search for one-way flight options from Springfield to Chicago. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 3/310:19 am
BDL
- ORD
1 stop30h 33m
Frontier
Deal found 1/31![Frontier logo]()
$60
This Gotogate deal was found by Cheapflights users on 2/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:19 am
BDL
- MDW
1 stop29h 07m
Frontier
Deal found 2/2![Frontier logo]()
$70
This Mytrip deal was found by Cheapflights users on 2/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:19 am
BDL
- ORD
1 stop25h 27m
Frontier
Deal found 2/1![Frontier logo]()
$70
This JetBlue deal was found by Cheapflights users on 2/1. 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.
Tue 2/246:00 am
BDL
- ORD
1 stop6h 59m
JetBlue
Deal found 2/1![JetBlue logo]()
$72
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:19 am
BDL
- MDW
1 stop29h 07m
Frontier
Deal found 2/1![Frontier logo]()
$74
This Priceline deal was found by Cheapflights users on 1/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/262:27 pm
BDL
- ORD
1 stop9h 12m
Frontier
Deal found 1/31![Frontier logo]()
$74
This Frontier deal was found by Cheapflights users on 1/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:52 am
BDL
- ORD
1 stop13h 23m
Frontier
Deal found 1/31![Frontier logo]()
$79
This Frontier deal was found by Cheapflights users on 2/2. 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.
Thu 2/262:27 pm
BDL
- MDW
1 stop9h 02m
Frontier
Deal found 2/2![Frontier logo]()
$80
This Booking.com deal was found by Cheapflights users on 2/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:27 pm
BDL
- ORD
1 stop9h 12m
Frontier
Deal found 2/1![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/98:08 pm
BDL
- MDW
1 stop23h 05m
Frontier
Deal found 2/2![Frontier logo]()
$81
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:27 pm
BDL
- MDW
1 stop9h 10m
Frontier
Deal found 2/1![Frontier logo]()
$84
This JetBlue deal was found by Cheapflights users on 2/1. 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 2/276:00 am
BDL
- ORD
1 stop6h 54m
JetBlue
Deal found 2/1![JetBlue logo]()
$84
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 February 2, 2026.
Round-trip from | $244 (Frontier) |
|---|---|
One-way from | $60 (Kiwi.com) |
Popular in | May |
Cheapest in | October |
Average price | $361 |
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 February 2, 2026.
Use the filters below to find and compare flights from Springfield to Chicago that are best for you.
Fly from
Springfield
Fly to
Chicago
Route
Depart
Return
Price
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Wed 7/29
5:04 pm-6:51 pm
Nonstop2h 47m
Chicago O'Hare Intl
Sat 8/1
6:30 pm-9:52 pm
Nonstop2h 22m
$300
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Fri 3/13
8:08 pm-11:38 pm
1 stop28h 30m
Chicago O'Hare Intl
Wed 3/18
6:10 pm-7:13 pm
2 stops24h 03m
$301
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Wed 3/4
5:30 am-7:05 am
Nonstop2h 35m
Chicago Midway
Wed 3/11
7:40 am-10:40 am
Nonstop2h 00m
$326
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Wed 3/4
10:05 am-11:57 am
Nonstop2h 52m
Chicago O'Hare Intl
Wed 3/11
6:05 pm-9:16 pm
Nonstop2h 11m
$326
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sat 2/28
5:00 am-6:35 am
Nonstop2h 35m
Chicago Midway
Sun 3/1
9:35 am-12:35 pm
Nonstop2h 00m
$343
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sun 2/15
2:27 pm-10:25 pm
1 stop8h 58m
Chicago Midway
Thu 2/19
7:30 am-4:55 pm
1 stop8h 25m
$345
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sat 3/21
7:15 am-8:45 am
Nonstop2h 30m
Chicago Midway
Tue 3/24
12:55 pm-3:55 pm
Nonstop2h 00m
$350
HartfordChicago
BDL - ORD
BDLORD
Hartford Bradley Intl
Sat 2/28
4:43 pm-6:35 pm
Nonstop2h 52m
Chicago O'Hare Intl
Sun 3/1
8:50 am-2:04 pm
1 stop4h 14m
$353
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Sat 5/9
4:55 pm-8:40 pm
1 stop4h 45m
Chicago Midway
Mon 5/11
3:50 pm-11:10 pm
2 stops6h 20m
$353
HartfordChicago
BDL - MDW
BDLMDW
Hartford Bradley Intl
Wed 5/13
12:25 pm-1:50 pm
Nonstop2h 25m
Chicago Midway
Sat 5/16
11:25 am-8:05 pm
1 stop7h 40m
$358
Showing 1-10 of 54 results
Best time to book a flight from Springfield to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Springfield with our price prediction graph.
BDL-MDW
BDL-ORD
BDL-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Springfield to Chicago
SFY-CHI
BDL-MDW
BDL-ORD
BDL-RFD
How far ahead should I book a flight from Springfield to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Springfield to Chicago. Price data was last updated on January 30, 2026.
To ensure you get the cheapest price possible for a flight from Springfield to Chicago, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 February 2, 2026.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Springfield to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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