$76+ Cheap flights from Valparaiso, FL (VPS) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Oct 13 — Oct 201
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Valparaiso to ChicagoExplore the most affordable flight options available from Valparaiso to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 13, 2026.
Explore the most affordable flight options available from Valparaiso to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 13, 2026.
This Kissandfly.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:50 pm -
Nonstop2h 18m
Mon 11/26:44 pm -
Nonstop2h 11m
Deal found 9/11![Allegiant Air logo]()
$83
This CheapOair deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/137:30 am -
Nonstop2h 18m
Mon 11/161:08 pm -
Nonstop2h 11m
Deal found 9/11![Allegiant Air logo]()
$91
This Cheapflightsfares deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:17 pm -
Nonstop2h 18m
Mon 10/266:44 pm -
Nonstop2h 11m
Deal found 9/11![Allegiant Air logo]()
$127
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/137:30 am -
Nonstop2h 18m
Thu 11/199:44 am -
Nonstop2h 05m
Deal found 9/10![Allegiant Air logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:37 pm -
Nonstop2h 24m
Sat 11/289:22 pm -
Nonstop2h 05m
Deal found 9/8![Allegiant Air logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:12 pm -
Nonstop2h 18m
Mon 10/196:15 pm -
Nonstop2h 11m
Deal found 9/12![Allegiant Air logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/131:39 pm -
2 stops28h 08m
Mon 11/161:08 pm -
Nonstop2h 11m
Deal found 9/11![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/305:50 pm -
Nonstop2h 18m
Mon 11/26:16 am -
2 stops10h 20m
Deal found 9/11![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/137:30 am -
Nonstop2h 18m
Thu 11/196:16 am -
2 stops30h 02m
Deal found 9/10![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:19 pm -
2 stops21h 32m
Mon 10/59:02 pm -
Nonstop2h 11m
Deal found 9/9![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Thu 10/17:00 am -
1 stop17h 23m
Sun 10/46:30 am -
1 stop17h 07m
Deal found 9/8![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
1 stop17h 23m
Mon 10/510:26 am -
2 stops9h 51m
Deal found 9/9![Multiple Airlines logo]()
$347
Best flights from Valparaiso to ChicagoDiscover carefully curated flight deals from Valparaiso to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 13, 2026.
Discover carefully curated flight deals from Valparaiso to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 13, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:12 pm -
Nonstop2h 18m
Mon 10/196:15 pm -
Nonstop2h 11m
Deal found 9/12![Allegiant Air logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/305:50 pm -
Nonstop2h 18m
Mon 11/26:16 am -
2 stops10h 20m
Deal found 9/11![Multiple Airlines logo]()
$261
This Sun Country Air deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2511:25 am -
1 stop7h 20m
Thu 12/3111:53 am -
1 stop5h 31m
Deal found 9/8![Sun Country Air logo]()
$354
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/132:10 pm -
1 stop6h 40m
Thu 11/195:20 pm -
1 stop3h 55m
Deal found 9/10![Southwest logo]()
$433
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:09 pm -
1 stop4h 21m
Fri 1/17:30 am -
1 stop8h 59m
Deal found 9/8![Delta logo]()
$463
This American Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Fri 3/124:40 pm -
1 stop7h 22m
Mon 3/159:06 am -
Nonstop2h 35m
Deal found 9/12![American Airlines logo]()
$494
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/96:15 am -
1 stop5h 21m
Mon 10/266:44 pm -
Nonstop2h 11m
Deal found 9/11![Allegiant Air logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:00 am -
3 stops51h 33m
Sat 11/289:22 pm -
Nonstop2h 05m
Deal found 9/11![Multiple Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/1310:25 am -
2 stops7h 10m
Mon 11/1611:30 am -
2 stops9h 45m
Deal found 9/11![Southwest logo]()
$462
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/259:31 am -
2 stops11h 15m
Thu 12/317:30 am -
1 stop6h 49m
Deal found 9/8![Delta logo]()
$498
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/86:04 pm -
1 stop6h 04m
Tue 10/135:29 pm -
1 stop6h 19m
Deal found 9/11![American Airlines logo]()
$503
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/307:25 am -
2 stops7h 30m
Mon 11/210:40 am -
2 stops10h 20m
Deal found 9/11![Southwest logo]()
$462
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/162:46 pm -
1 stop5h 52m
Mon 10/196:30 am -
1 stop4h 29m
Deal found 9/12![Delta logo]()
$503
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/164:40 pm -
1 stop5h 20m
Mon 10/197:25 am -
1 stop5h 45m
Deal found 9/12![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:00 am -
1 stop4h 54m
Tue 10/135:09 pm -
1 stop6h 10m
Deal found 9/11![Delta logo]()
$503
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:00 am -
2 stops14h 46m
Tue 12/298:05 am -
1 stop12h 35m
Deal found 9/8![Delta logo]()
$519
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/259:31 am -
2 stops11h 15m
Mon 12/285:30 am -
1 stop13h 26m
Deal found 9/8![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/167:00 am -
1 stop7h 28m
Sun 10/185:27 am -
1 stop5h 32m
Deal found 9/12![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:30 pm -
1 stop4h 24m
Sat 11/285:30 am -
1 stop5h 41m
Deal found 9/9![Delta logo]()
$570
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 1/19:31 am -
1 stop10h 28m
Mon 1/47:00 am -
2 stops14h 57m
Deal found 9/10![Delta logo]()
$629
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 1/27:41 pm -
1 stop4h 18m
Mon 1/47:10 am -
1 stop4h 03m
Deal found 9/10![Delta logo]()
$800
Last-minute flights from Valparaiso to ChicagoDiscover last-minute flight deals from Valparaiso to Chicago. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Valparaiso to Chicago. Data last updated September 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:19 pm -
2 stops21h 32m
Mon 10/59:02 pm -
Nonstop2h 11m
Deal found 9/9![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Thu 10/17:00 am -
1 stop17h 23m
Sun 10/46:30 am -
1 stop17h 07m
Deal found 9/8![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:01 pm -
1 stop20h 33m
Mon 10/59:02 pm -
Nonstop2h 11m
Deal found 9/9![Allegiant Air logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
1 stop17h 23m
Mon 10/510:26 am -
2 stops9h 51m
Deal found 9/9![Multiple Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:00 pm -
2 stops8h 15m
Mon 10/511:05 am -
2 stops9h 55m
Deal found 9/9![Southwest logo]()
$392
This Cheapflightsfares deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:17 pm -
Nonstop2h 18m
Mon 10/266:44 pm -
Nonstop2h 11m
Deal found 9/11![Allegiant Air logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:12 pm -
Nonstop2h 18m
Mon 10/196:15 pm -
Nonstop2h 11m
Deal found 9/12![Allegiant Air logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:07 pm -
Nonstop2h 18m
Thu 10/226:40 pm -
2 stops24h 34m
Deal found 9/9![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:27 pm -
2 stops23h 04m
Thu 10/226:30 am -
1 stop17h 07m
Deal found 9/9![Multiple Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:15 am -
1 stop3h 40m
Wed 11/45:20 pm -
1 stop3h 55m
Deal found 9/9![Southwest logo]()
$371
This Kissandfly.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:50 pm -
Nonstop2h 18m
Mon 11/26:44 pm -
Nonstop2h 11m
Deal found 9/11![Allegiant Air logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/305:50 pm -
Nonstop2h 18m
Mon 11/26:16 am -
2 stops10h 20m
Deal found 9/11![Multiple Airlines logo]()
$261
One-way flights from Valparaiso to ChicagoSearch for one-way flight options from Valparaiso to Chicago. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
Search for one-way flight options from Valparaiso to Chicago. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 11/23:36 pm -
Nonstop2h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$76
This Sun Country Air deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:35 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Sun Country Air logo]()
$141
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:07 pm -
Nonstop2h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$148
This Sun Country Air deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:35 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Sun Country Air logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:11 pm -
2 stops40h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/122:52 pm -
2 stops45h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/131:39 pm -
2 stops23h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 12/108:43 am -
2 stops22h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:43 am -
2 stops22h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$178
This CheapOair deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Mon 10/263:36 pm -
Nonstop2h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Allegiant Air logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/117:55 am -
1 stop16h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$181
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/217:15 am -
1 stop3h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Southwest logo]()
$183
Find flight deals from Valparaiso to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $83 (Kissandfly.com) |
One-way from | $76 (CheapOair) |
Popular in | September |
Cheapest in | August |
Average price | $496 |
Good round-trip deal | $118 or less |
Good one-way deal | $404 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Valparaiso 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 7,457,451 searches. Data last updated September 13, 2026.
Use the filters below to find and compare flights from Valparaiso to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 11/12
10:35 am-6:35 pm
1 stop8h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$151
Quickest round-trip
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 10/26
3:36 pm-5:54 pm
Nonstop2h 18m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$180
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 10/16
6:12 pm-8:30 pm
Nonstop2h 18m
Chicago Midway
Mon 10/19
6:15 pm-8:26 pm
Nonstop2h 11m
$180
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 12/12
1:00 pm-7:35 pm
1 stop6h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$187
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 12/11
10:25 am-8:25 pm
2 stops10h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$212
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 10/10
5:50 pm-9:45 pm
1 stop3h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$225
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 10/10
7:00 am-5:45 pm
2 stops34h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$238
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 9/19
10:55 am-8:35 pm
2 stops9h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$250
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 10/30
5:50 pm-8:08 pm
Nonstop2h 18m
Chicago Midway
Mon 11/2
6:16 am-4:36 pm
2 stops10h 20m
$261
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 12/10
7:00 am-2:49 pm
1 stop7h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$296
Showing 1-10 of 40 resultsSorted by cheapest first
Compare providers for flights from Valparaiso to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Valparaiso to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Valparaiso, Florida-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Valparaiso, Florida-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Valparaiso, Florida-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Valparaiso, Florida-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Valparaiso, Florida-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Valparaiso to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Valparaiso with our price prediction graph.
VPS-CHI
VPS-MDW
VPS-ORD
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 Valparaiso to Chicago
VPS-CHI
VPS-MDW
VPS-ORD
What is the cheapest month to book a flight from Valparaiso, Florida to Chicago?
Currently, August is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $139). Flying from Valparaiso, Florida to Chicago in September is currently the most expensive (average of $496). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Valparaiso, Florida to Chicago?
Airfare is below average for this route at the moment.
Valparaiso, Florida to Chicago flights typically cost between $401 and $496 in October.The cheapest round-trip price found within the last 5 days was $83 on Allegiant Air (Oct 30-Nov 2).
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 September 13, 2026.
Get a feel of what it's like to fly with Allegiant Air and American Airlines from Valparaiso to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Overall
7.3
Comfort
6.9
Entertainment
5.4
Food
5.9
Crew
8.1
Reviews
1 / 20
2.0
MediocreNic,Aug 2026
SRQ - ALB
Boarding
7.7
Overall
7.3
Comfort
6.9
Entertainment
5.4
Food
5.9
Crew
8.1
Reviews
1 / 20
2.0
MediocreNic,Aug 2026
SRQ - ALB
Boarding
7.7
Overall
7.3
Comfort
6.9
Entertainment
5.4
Food
5.9
Crew
8.1
Reviews
1 / 20
2.0
MediocreNic,Aug 2026
SRQ - ALB
Related info for your journey
Find useful and relevant information for your journey from Valparaiso 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
Merrillville
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Valparaiso
Hammond
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Valparaiso and Chicago flights
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Top 2 airlines flying from Valparaiso to Chicago
Discover the top 2 airlines that operate flights from Valparaiso to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$158 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$295 | Average$467 | FlexibilityNo cancel fee | On-time71% |