$139+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Sep 7 — Sep 141
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
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 January or October, booked 85 days in advance, depart on a Wednesday or Saturday and return on a Saturday
Cheap flight deals from Springfield to Chicago
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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 August 8, 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 August 8, 2026.
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:07 pm -
1 stop7h 37m
Wed 8/2612:44 am -
1 stop11h 03m
Deal found 8/6![Multiple Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:52 pm -
Nonstop2h 57m
Sun 9/67:29 pm -
Nonstop2h 19m
Deal found 8/4![American Airlines logo]()
$278
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:25 am -
1 stop6h 22m
Wed 11/42:35 pm -
1 stop8h 20m
Deal found 8/5![JetBlue logo]()
$281
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:16 pm -
1 stop8h 43m
Thu 10/86:05 am -
1 stop12h 55m
Deal found 8/7![Frontier logo]()
$282
This Travelocity deal was found by Cheapflights users on 8/7. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:25 am -
1 stop4h 34m
Thu 10/86:05 am -
1 stop12h 55m
Deal found 8/7![Multiple Airlines logo]()
$284
This Super.com deal was found by Cheapflights users on 8/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:55 pm -
1 stop17h 21m
Sun 10/186:05 am -
1 stop12h 55m
Deal found 8/7![Frontier logo]()
$285
This Priceline deal was found by Cheapflights users on 8/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:16 pm -
1 stop8h 43m
Mon 10/53:00 pm -
1 stop7h 14m
Deal found 8/8![Multiple Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:50 pm -
Nonstop2h 25m
Sun 9/67:45 am -
1 stop6h 35m
Deal found 8/4![Southwest logo]()
$287
This Priceline deal was found by Cheapflights users on 8/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:42 pm -
1 stop10h 45m
Sat 8/2912:44 am -
1 stop11h 03m
Deal found 8/5![Frontier logo]()
$288
This Frontier deal was found by Cheapflights users on 8/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:16 pm -
1 stop8h 43m
Sun 10/116:05 am -
1 stop12h 55m
Deal found 8/6![Frontier logo]()
$290
This Priceline deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:07 pm -
1 stop7h 37m
Sat 8/2912:44 am -
1 stop11h 03m
Deal found 8/4![Multiple Airlines logo]()
$292
This Priceline deal was found by Cheapflights users on 8/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:42 pm -
1 stop10h 45m
Sun 9/612:44 am -
1 stop11h 03m
Deal found 8/7![Frontier logo]()
$293
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 August 8, 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 August 8, 2026.
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am -
1 stop7h 45m
Sun 9/273:00 pm -
1 stop7h 14m
Deal found 8/4![JetBlue logo]()
$299
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:50 pm -
Nonstop2h 25m
Tue 9/298:45 am -
Nonstop2h 15m
Deal found 8/5![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:20 am -
1 stop5h 27m
Sat 10/106:44 pm -
1 stop3h 48m
Deal found 8/3![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1312:38 pm -
Nonstop2h 45m
Fri 10/167:30 am -
Nonstop2h 19m
Deal found 8/3![United Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
1 stop13h 06m
Sun 11/110:20 am -
2 stops23h 35m
Deal found 8/3![Multiple Airlines logo]()
$361
This JetBlue deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:25 am -
1 stop4h 33m
Sun 9/133:00 pm -
1 stop7h 14m
Deal found 8/6![JetBlue logo]()
$311
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
Nonstop2h 25m
Mon 9/141:10 pm -
Nonstop2h 05m
Deal found 8/4![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:23 am -
1 stop4h 54m
Wed 10/1410:59 am -
1 stop6h 05m
Deal found 8/6![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:50 pm -
Nonstop2h 25m
Thu 9/38:45 am -
Nonstop2h 15m
Deal found 8/4![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:50 pm -
Nonstop2h 45m
Fri 9/187:15 am -
Nonstop2h 19m
Deal found 8/4![United Airlines logo]()
$347
This JetBlue deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:25 am -
1 stop4h 33m
Sun 9/203:00 pm -
1 stop7h 14m
Deal found 8/6![JetBlue logo]()
$341
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:55 am -
Nonstop2h 20m
Tue 9/156:25 pm -
Nonstop2h 10m
Deal found 8/3![Southwest logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:00 am -
1 stop28h 05m
Fri 9/185:05 pm -
1 stop16h 51m
Deal found 8/5![Multiple Airlines logo]()
$382
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:37 am -
1 stop7h 21m
Mon 11/166:25 pm -
Nonstop2h 22m
Deal found 8/3![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 8/6. 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.
Sat 8/293:50 pm -
Nonstop2h 25m
Mon 8/317:10 pm -
Nonstop2h 05m
Deal found 8/6![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Fri 9/47:55 pm -
1 stop4h 45m
Mon 9/76:15 pm -
Nonstop2h 23m
Deal found 8/7![United Airlines logo]()
$357
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:25 am -
1 stop4h 33m
Tue 10/63:00 pm -
1 stop7h 14m
Deal found 8/4![JetBlue logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Thu 8/207:02 am -
2 stops9h 07m
Mon 8/246:56 pm -
1 stop18h 54m
Deal found 8/7![Multiple Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 8/8. 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 9/57:55 am -
Nonstop2h 20m
Sat 9/123:25 pm -
Nonstop2h 05m
Deal found 8/8![Southwest logo]()
$324
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
1 stop4h 38m
Tue 9/292:30 pm -
Nonstop2h 23m
Deal found 8/4![United Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 8/237:02 am -
2 stops9h 07m
Mon 8/246:56 pm -
1 stop18h 54m
Deal found 8/5![Multiple Airlines logo]()
$404
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:07 pm -
1 stop7h 37m
Sun 8/235:27 pm -
1 stop5h 53m
Deal found 8/5![JetBlue logo]()
$385
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:40 pm -
Nonstop2h 15m
Wed 9/308:55 am -
2 stops7h 30m
Deal found 8/4![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
1 stop6h 46m
Sun 10/187:30 am -
Nonstop2h 19m
Deal found 8/4![United Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:16 pm -
1 stop18h 36m
Thu 9/173:53 pm -
2 stops21h 00m
Deal found 8/4![Multiple Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:05 am -
1 stop9h 40m
Mon 9/211:20 pm -
2 stops7h 55m
Deal found 8/4![Southwest logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:00 am -
1 stop13h 08m
Mon 11/167:03 pm -
2 stops27h 28m
Deal found 8/3![Multiple Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:40 pm -
1 stop6h 20m
Tue 9/158:35 am -
2 stops5h 15m
Deal found 8/3![Southwest logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:16 pm -
1 stop18h 36m
Mon 9/284:50 pm -
2 stops23h 18m
Deal found 8/4![Multiple Airlines logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/97:00 am -
1 stop13h 12m
Mon 10/1210:39 am -
2 stops29h 29m
Deal found 8/5![Multiple Airlines logo]()
$487
Last-minute flights from Springfield to ChicagoDiscover last-minute flight deals from Springfield to Chicago. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Chicago. Data last updated August 8, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:07 pm -
1 stop7h 37m
Thu 8/205:27 pm -
1 stop5h 53m
Deal found 8/4![JetBlue logo]()
$295
This JetBlue deal was found by Cheapflights users on 8/6. 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.
Sun 8/235:07 pm -
1 stop7h 37m
Fri 8/285:27 pm -
1 stop5h 53m
Deal found 8/6![JetBlue logo]()
$299
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:07 pm -
1 stop7h 37m
Wed 8/2612:44 am -
1 stop11h 03m
Deal found 8/6![Multiple Airlines logo]()
$277
This Justfly.com deal was found by Cheapflights users on 8/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:07 pm -
1 stop7h 37m
Fri 8/282:35 pm -
1 stop8h 23m
Deal found 8/5![JetBlue logo]()
$281
This Priceline deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:07 pm -
1 stop7h 37m
Sat 8/2912:44 am -
1 stop11h 03m
Deal found 8/4![Multiple Airlines logo]()
$292
This Priceline deal was found by Cheapflights users on 8/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:42 pm -
1 stop10h 45m
Sat 8/2912:44 am -
1 stop11h 03m
Deal found 8/5![Frontier logo]()
$288
This Priceline deal was found by Cheapflights users on 8/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:42 pm -
1 stop10h 45m
Sun 9/612:44 am -
1 stop11h 03m
Deal found 8/7![Frontier logo]()
$293
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:52 pm -
Nonstop2h 57m
Sun 9/67:29 pm -
Nonstop2h 19m
Deal found 8/4![American Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:50 pm -
Nonstop2h 25m
Sun 9/67:45 am -
1 stop6h 35m
Deal found 8/4![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/7. 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.
Sat 9/53:50 pm -
Nonstop2h 25m
Tue 9/88:45 am -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$296
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Sat 9/511:44 am -
Nonstop2h 45m
Tue 9/82:25 pm -
Nonstop2h 20m
Deal found 8/7![United Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Tue 9/227:05 am -
2 stops12h 18m
Thu 9/243:50 pm -
1 stop21h 28m
Deal found 8/8![Multiple Airlines logo]()
$298
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 August 8, 2026.
Search for one-way flight options from Springfield to Chicago. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
This Southwest deal was found by Cheapflights users on 8/7. 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.
Sat 9/57:55 am -
Nonstop2h 20m
Deal found 8/7![Southwest logo]()
$139
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Sat 9/54:50 pm -
Nonstop2h 45m
Deal found 8/7![United Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Mon 8/317:11 pm -
3 stops25h 57m
Deal found 8/8![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Sun 10/43:16 pm -
2 stops28h 07m
Deal found 8/8![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Mon 11/98:55 pm -
1 stop27h 55m
Deal found 8/7![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am -
2 stops34h 20m
Deal found 8/4![Multiple Airlines logo]()
$143
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:55 pm -
1 stop12h 26m
Deal found 8/7![Frontier logo]()
$144
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:07 pm -
1 stop7h 37m
Deal found 8/4![JetBlue logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/133:16 pm -
1 stop19h 16m
Deal found 8/4![Multiple Airlines logo]()
$148
This JetBlue deal was found by Cheapflights users on 8/7. 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.
Sat 8/225:07 pm -
1 stop7h 37m
Deal found 8/7![JetBlue logo]()
$148
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:09 pm -
1 stop4h 50m
Deal found 8/7![Delta logo]()
$149
This Priceline deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/71:42 pm -
1 stop10h 45m
Deal found 8/4![Frontier 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 August 8, 2026.
Round-trip from | $277 (American Airlines) |
|---|---|
One-way from | $139 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $377 |
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 August 8, 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
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Wed 9/23
7:00 am-1:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Sun 9/27
3:00 pm-11:14 pm
1 stop7h 14m
$299
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Fri 9/11
6:25 am-9:58 am
1 stop4h 33m
Chicago O'Hare Intl
Sun 9/13
3:00 pm-11:14 pm
1 stop7h 14m
$311
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 9/26
3:50 pm-5:15 pm
Nonstop2h 25m
Chicago Midway
Tue 9/29
8:45 am-12:00 pm
Nonstop2h 15m
$315
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 9/12
3:50 pm-5:15 pm
Nonstop2h 25m
Chicago Midway
Mon 9/14
1:10 pm-4:15 pm
Nonstop2h 05m
$315
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 8/29
3:50 pm-5:15 pm
Nonstop2h 25m
Chicago Midway
Thu 9/3
8:45 am-12:00 pm
Nonstop2h 15m
$315
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 9/12
7:55 am-9:15 am
Nonstop2h 20m
Chicago Midway
Tue 9/15
6:25 pm-9:35 pm
Nonstop2h 10m
$315
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 8/29
3:50 pm-5:15 pm
Nonstop2h 25m
Chicago Midway
Mon 8/31
7:10 pm-10:15 pm
Nonstop2h 05m
$315
Quickest round-trip
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 9/5
7:55 am-9:15 am
Nonstop2h 20m
Chicago Midway
Sat 9/12
3:25 pm-6:30 pm
Nonstop2h 05m
$324
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Mon 9/28
1:40 pm-2:55 pm
Nonstop2h 15m
Chicago Midway
Wed 9/30
8:55 am-5:25 pm
2 stops7h 30m
$330
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 10/6
7:20 am-11:47 am
1 stop5h 27m
Chicago Midway
Sat 10/10
6:44 pm-11:32 pm
1 stop3h 48m
$335
Showing 1-10 of 58 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-MDW
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-ORD
BDL-MDW
BDL-RFD
How much does it cost to fly round-trip from Springfield to Chicago?
Airfare is below average for this route at the moment.
Springfield to Chicago flights typically cost between $333 and $448 in August.The cheapest round-trip price found within the last 5 days was $277 on Multiple Airlines (Aug 24-Aug 26).
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 August 8, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Valparaiso
Hammond
Saint Joseph
Porter
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