$85+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI
Jul 23 — Jul 301
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
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 June 23, 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 June 23, 2026.
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/15:45 pm
MDW
- BDL
Nonstop2h 10m
Southwest
Sat 8/153:50 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Deal found 6/22![Southwest logo]()
$325
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:30 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Mon 10/195:03 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 6/21![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:50 am
MDW
- BDL
Nonstop2h 15m
Southwest
Mon 8/106:20 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Deal found 6/19![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:00 pm
ORD
- BDL
1 stop7h 25m
Delta
Mon 8/175:16 pm
BDL
- ORD
1 stop7h 41m
Delta
Deal found 6/20![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Mon 8/106:50 am
BDL
- MDW
1 stop7h 20m
Delta
Deal found 6/19![Delta logo]()
$328
This Priceline deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:22 pm
ORD
- BDL
1 stop5h 37m
Multiple Airlines
Sun 7/51:42 pm
BDL
- ORD
1 stop10h 45m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:31 pm
ORD
- BDL
Nonstop2h 27m
American Airlines
Tue 10/66:00 am
BDL
- ORD
1 stop5h 16m
American Airlines
Deal found 6/18![American Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/159:05 am
MDW
- BDL
1 stop5h 05m
Southwest
Tue 8/1812:40 pm
BDL
- MDW
2 stops7h 45m
Southwest
Deal found 6/22![Southwest logo]()
$333
This Priceline deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Fri 7/101:42 pm
BDL
- ORD
1 stop10h 45m
Frontier
Deal found 6/18![Frontier logo]()
$334
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/41:34 pm
ORD
- BDL
Nonstop2h 24m
American Airlines
Sat 7/256:50 pm
BDL
- ORD
1 stop5h 40m
American Airlines
Deal found 6/19![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:46 am
ORD
- BDL
1 stop4h 32m
American Airlines
Thu 9/241:12 pm
BDL
- ORD
Nonstop2h 48m
American Airlines
Deal found 6/18![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:15 pm
ORD
- BDL
Nonstop2h 10m
American Airlines
Mon 10/197:30 pm
BDL
- ORD
1 stop4h 51m
American Airlines
Deal found 6/21![American Airlines logo]()
$337
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 June 23, 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 June 23, 2026.
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/14:50 pm
MDW
- BDL
1 stop5h 35m
Southwest
Sat 8/153:50 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Deal found 6/22![Southwest logo]()
$335
This JetBlue deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:35 pm
ORD
- BDL
1 stop8h 20m
JetBlue
Mon 10/196:25 am
BDL
- ORD
1 stop6h 22m
JetBlue
Deal found 6/20![JetBlue logo]()
$344
This American Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/268:10 am
ORD
- BDL
Nonstop2h 26m
American Airlines
Sun 8/305:40 pm
BDL
- ORD
Nonstop3h 09m
American Airlines
Deal found 6/22![American Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:10 am
ORD
- BDL
1 stop7h 54m
Delta
Sat 10/175:05 pm
BDL
- ORD
1 stop5h 40m
Delta
Deal found 6/22![Delta logo]()
$367
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 9/13:00 pm
ORD
- BDL
Nonstop2h 20m
United Airlines
Wed 9/211:44 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 6/22![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:45 am
MDW
- BDL
Nonstop2h 15m
Southwest
Fri 8/146:20 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Deal found 6/21![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/2610:10 am
MDW
- BDL
2 stops10h 00m
Southwest
Sun 8/307:50 am
BDL
- MDW
Nonstop2h 20m
Southwest
Deal found 6/22![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/83:00 pm
ORD
- BDL
Nonstop2h 37m
United Airlines
Mon 8/107:45 pm
BDL
- ORD
1 stop4h 46m
United Airlines
Deal found 6/21![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:35 pm
ORD
- BDL
1 stop5h 27m
Delta
Mon 11/96:00 am
BDL
- ORD
1 stop7h 06m
Delta
Deal found 6/18![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:45 am
ORD
- BDL
1 stop7h 14m
Delta
Sun 7/261:15 pm
BDL
- ORD
1 stop6h 14m
Delta
Deal found 6/19![Delta logo]()
$403
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/146:15 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Sun 8/164:50 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 6/22![United Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:30 am
MDW
- BDL
1 stop4h 30m
Southwest
Tue 9/85:55 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Deal found 6/18![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/146:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Sun 8/1612:55 pm
BDL
- MDW
1 stop6h 38m
Delta
Deal found 6/22![Delta logo]()
$425
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:25 pm
MDW
- BDL
1 stop3h 45m
Southwest
Mon 8/316:20 am
BDL
- MDW
2 stops9h 10m
Southwest
Deal found 6/21![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:00 pm
MDW
- BDL
1 stop4h 20m
Southwest
Thu 7/237:10 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Deal found 6/20![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:50 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Wed 7/222:35 pm
BDL
- MDW
1 stop4h 20m
Southwest
Deal found 6/20![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:00 am
MDW
- BDL
1 stop6h 05m
Southwest
Mon 8/105:55 am
BDL
- MDW
2 stops9h 15m
Southwest
Deal found 6/19![Southwest logo]()
$430
Last-minute flights from Chicago to SpringfieldDiscover last-minute flight deals from Chicago to Springfield. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Springfield. Data last updated June 23, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:22 pm
ORD
- BDL
1 stop5h 37m
Multiple Airlines
Sun 7/51:42 pm
BDL
- ORD
1 stop10h 45m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$329
This Priceline deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:22 pm
ORD
- BDL
1 stop5h 37m
Multiple Airlines
Tue 7/71:42 pm
BDL
- ORD
1 stop10h 45m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/41:34 pm
ORD
- BDL
Nonstop2h 24m
American Airlines
Sat 7/256:50 pm
BDL
- ORD
1 stop5h 40m
American Airlines
Deal found 6/19![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:16 pm
ORD
- BDL
Nonstop2h 22m
American Airlines
Thu 10/227:23 am
BDL
- ORD
Nonstop2h 42m
American Airlines
Deal found 6/21![American Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/43:25 pm
ORD
- BDL
1 stop5h 20m
Delta
Sat 7/255:30 am
BDL
- ORD
1 stop6h 02m
Delta
Deal found 6/22![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/410:55 am
MDW
- BDL
1 stop6h 15m
Delta
Sat 7/251:15 pm
BDL
- MDW
1 stop5h 52m
Delta
Deal found 6/22![Delta logo]()
$345
This Priceline deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/512:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Fri 7/101:42 pm
BDL
- ORD
1 stop10h 45m
Frontier
Deal found 6/19![Frontier logo]()
$343
This Priceline deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Fri 7/101:42 pm
BDL
- ORD
1 stop10h 45m
Frontier
Deal found 6/18![Frontier logo]()
$334
This Travelocity deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity 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 44m
Multiple Airlines
Sun 7/121:42 pm
BDL
- ORD
1 stop10h 45m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$340
This CheapOair deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:00 am
ORD
- BDL
2 stops15h 59m
Multiple Airlines
Wed 7/1512:27 pm
BDL
- ORD
1 stop11h 43m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:54 am
MDW
- BDL
1 stop7h 10m
Delta
Wed 7/226:00 am
BDL
- MDW
1 stop5h 05m
Delta
Deal found 6/18![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:10 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Sat 7/2512:12 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 6/20![United Airlines logo]()
$347
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 June 23, 2026.
Search for one-way flight options from Chicago to Springfield. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This CheapOair deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:30 pm
ORD
- BDL
1 stop4h 50m
JetBlue
Deal found 6/22![JetBlue logo]()
$85
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:27 pm
ORD
- BDL
1 stop5h 53m
JetBlue
Deal found 6/22![JetBlue logo]()
$93
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/175:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 6/22![JetBlue logo]()
$101
This Priceline deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Mon 7/1312:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Deal found 6/22![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/1212:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Deal found 6/22![Frontier logo]()
$132
This Priceline deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:44 am
ORD
- BDL
1 stop11h 03m
Frontier
Deal found 6/22![Frontier logo]()
$143
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/147:00 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Deal found 6/22![United Airlines logo]()
$145
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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
Deal found 6/22![Southwest logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/215:13 pm
ORD
- BDL
1 stop17h 19m
Frontier
Deal found 6/22![Frontier logo]()
$148
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:04 pm
ORD
- BDL
Nonstop2h 22m
American Airlines
Deal found 6/21![American Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:03 pm
MDW
- BDL
2 stops10h 41m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$153
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/296:00 am
MDW
- BDL
1 stop5h 45m
Delta
Deal found 6/22![Delta logo]()
$155
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 June 23, 2026.
Round-trip from | $325 (Southwest) |
|---|---|
One-way from | $85 (CheapOair) |
Popular in | April |
Cheapest in | August |
Average price | $433 |
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 June 23, 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
Sat 8/1
4:50 pm-11:25 pm
1 stop5h 35m
Hartford Bradley Intl
Sat 8/15
3:50 pm-5:15 pm
Nonstop2h 25m
$335
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Thu 10/15
2:35 pm-11:55 pm
1 stop8h 20m
Hartford Bradley Intl
Mon 10/19
6:25 am-11:47 am
1 stop6h 22m
$344
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Wed 8/26
8:10 am-11:36 am
Nonstop2h 26m
Hartford Bradley Intl
Sun 8/30
5:40 pm-7:49 pm
Nonstop3h 09m
$347
Quickest round-trip
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Wed 8/12
8:45 am-12:00 pm
Nonstop2h 15m
Hartford Bradley Intl
Fri 8/14
6:20 pm-7:40 pm
Nonstop2h 20m
$347
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Wed 8/26
10:10 am-9:10 pm
2 stops10h 00m
Hartford Bradley Intl
Sun 8/30
7:50 am-9:10 am
Nonstop2h 20m
$362
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Sun 10/11
7:10 am-4:04 pm
1 stop7h 54m
Hartford Bradley Intl
Sat 10/17
5:05 pm-9:45 pm
1 stop5h 40m
$367
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Tue 9/1
3:00 pm-6:20 pm
Nonstop2h 20m
Hartford Bradley Intl
Wed 9/2
11:44 am-1:29 pm
Nonstop2h 45m
$369
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Fri 9/4
7:30 am-1:00 pm
1 stop4h 30m
Hartford Bradley Intl
Tue 9/8
5:55 pm-7:15 pm
Nonstop2h 20m
$371
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Fri 8/28
5:25 pm-10:10 pm
1 stop3h 45m
Hartford Bradley Intl
Mon 8/31
6:20 am-2:30 pm
2 stops9h 10m
$391
ChicagoHartford
ORD - BDL
ORDBDL
Chicago O'Hare Intl
Sat 8/8
3:00 pm-6:37 pm
Nonstop2h 37m
Hartford Bradley Intl
Mon 8/10
7:45 pm-11:31 pm
1 stop4h 46m
$399
Showing 1-10 of 36 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 June 23, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to Springfield. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Top destinations