$52+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Nov 30 — Dec 71
Round-trip
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Valparaiso to Chicago
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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 October 31, 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 October 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/23:36 pm -
Nonstop2h 18m
Fri 11/610:38 am -
Nonstop2h 11m
Deal found 10/27![Allegiant Air logo]()
$219
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:30 am -
Nonstop2h 18m
Fri 11/1310:38 am -
Nonstop2h 11m
Deal found 10/30![Allegiant Air logo]()
$223
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/811:10 am -
1 stop6h 00m
Thu 12/107:05 am -
1 stop6h 20m
Deal found 10/27![Southwest logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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
Tue 11/176:08 am -
3 stops54h 51m
Deal found 10/29![Multiple Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/72:05 pm -
1 stop8h 40m
Thu 12/107:05 am -
1 stop6h 20m
Deal found 10/27![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/11:46 pm -
1 stop22h 50m
Fri 11/610:38 am -
Nonstop2h 11m
Deal found 10/27![Allegiant Air logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/2511:37 am -
2 stops20h 37m
Mon 11/306:51 pm -
Nonstop2h 05m
Deal found 10/26![Multiple Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:05 pm -
1 stop8h 40m
Mon 12/75:25 pm -
1 stop3h 50m
Deal found 10/30![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/32:05 pm -
1 stop8h 40m
Sun 12/65:20 am -
1 stop8h 05m
Deal found 10/26![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
1 stop8h 49m
Sat 12/58:00 am -
1 stop8h 00m
Deal found 10/30![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:32 am -
1 stop7h 34m
Mon 12/76:49 am -
1 stop9h 11m
Deal found 10/30![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am -
1 stop5h 24m
Sat 12/56:16 pm -
1 stop14h 29m
Deal found 10/30![Delta logo]()
$435
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 October 31, 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 October 31, 2026.
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/811:10 am -
1 stop6h 00m
Thu 12/107:05 am -
1 stop6h 20m
Deal found 10/27![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
1 stop8h 49m
Sat 12/58:00 am -
1 stop8h 00m
Deal found 10/30![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/72:05 pm -
1 stop8h 40m
Thu 12/107:05 am -
1 stop6h 20m
Deal found 10/27![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:32 am -
1 stop9h 37m
Tue 12/81:34 pm -
1 stop9h 44m
Deal found 10/30![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/296:00 pm -
1 stop6h 20m
Fri 1/17:05 am -
1 stop6h 20m
Deal found 10/26![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:46 pm -
1 stop8h 08m
Wed 12/91:02 pm -
1 stop10h 16m
Deal found 10/30![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am -
1 stop9h 16m
Tue 12/81:02 pm -
1 stop10h 16m
Deal found 10/30![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:32 am -
1 stop7h 34m
Sat 12/58:00 am -
1 stop8h 00m
Deal found 10/30![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:30 pm -
1 stop14h 58m
Thu 12/101:02 pm -
1 stop7h 54m
Deal found 10/30![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:46 pm -
1 stop8h 08m
Mon 12/76:00 am -
1 stop7h 59m
Deal found 10/30![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/199:17 am -
1 stop6h 36m
Wed 1/277:10 am -
1 stop7h 02m
Deal found 10/27![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/207:05 am -
1 stop6h 22m
Wed 1/279:50 am -
1 stop4h 22m
Deal found 10/27![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/191:00 pm -
1 stop5h 48m
Thu 1/213:00 pm -
1 stop5h 57m
Deal found 10/27![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/191:00 pm -
1 stop5h 48m
Sun 1/249:50 am -
1 stop6h 33m
Deal found 10/27![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/295:12 pm -
1 stop6h 50m
Fri 1/19:00 am -
1 stop5h 18m
Deal found 10/26![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/209:17 am -
1 stop4h 10m
Fri 1/223:00 pm -
1 stop5h 57m
Deal found 10/27![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/269:17 am -
1 stop6h 36m
Fri 1/2911:20 am -
1 stop5h 03m
Deal found 10/27![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am -
1 stop4h 25m
Sun 12/66:49 am -
1 stop4h 24m
Deal found 10/30![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/136:00 am -
1 stop6h 20m
Sun 11/155:30 am -
1 stop5h 41m
Deal found 10/26![Delta logo]()
$581
Last-minute flights from Valparaiso to ChicagoDiscover last-minute flight deals from Valparaiso to Chicago. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Valparaiso to Chicago. Data last updated October 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/11:46 pm -
1 stop22h 50m
Fri 11/610:38 am -
Nonstop2h 11m
Deal found 10/27![Allegiant Air logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/23:36 pm -
Nonstop2h 18m
Fri 11/610:38 am -
Nonstop2h 11m
Deal found 10/27![Allegiant Air logo]()
$219
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/311:46 am -
Nonstop2h 49m
Tue 11/108:34 am -
Nonstop2h 35m
Deal found 10/26![American Airlines logo]()
$512
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/35:07 pm -
1 stop6h 50m
Tue 11/101:30 pm -
1 stop5h 13m
Deal found 10/26![Delta logo]()
$531
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:30 am -
Nonstop2h 18m
Fri 11/1310:38 am -
Nonstop2h 11m
Deal found 10/30![Allegiant Air logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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
Tue 11/176:08 am -
3 stops54h 51m
Deal found 10/29![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:30 am -
Nonstop2h 18m
Sun 11/156:08 am -
3 stops37h 37m
Deal found 10/30![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/196:30 am -
Nonstop2h 24m
Fri 11/201:06 pm -
2 stops47h 53m
Deal found 10/26![Multiple Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/2412:10 pm -
1 stop12h 10m
Tue 12/16:05 am -
1 stop9h 46m
Deal found 10/28![American Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/247:05 am -
1 stop5h 15m
Sat 11/286:49 am -
1 stop7h 10m
Deal found 10/26![Delta logo]()
$498
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2412:10 pm -
1 stop12h 10m
Sun 11/298:34 am -
Nonstop2h 36m
Deal found 10/30![American Airlines logo]()
$516
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/2511:37 am -
2 stops20h 37m
Mon 11/306:51 pm -
Nonstop2h 05m
Deal found 10/26![Multiple Airlines logo]()
$347
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 October 31, 2026.
Search for one-way flight options from Valparaiso to Chicago. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
This Jetabroad deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 am -
Nonstop2h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Allegiant Air logo]()
$52
This Super.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/67:30 am -
Nonstop2h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Allegiant Air logo]()
$99
This Jetabroad deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:55 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Sun Country Air logo]()
$149
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/2612:00 pm -
1 stop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/306:00 pm -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/296:00 pm -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/61:39 pm -
2 stops23h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/2912:03 pm -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/87:03 am -
1 stop11h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/157:00 am -
1 stop5h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Delta logo]()
$232
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:00 am -
1 stop6h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Delta logo]()
$232
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/267:11 am -
1 stop27h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$245
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 October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (Southwest) |
One-way from | $52 (Jetabroad) |
Popular in | October |
Cheapest in | August |
Average price | $543 |
Good round-trip deal | $161 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 October 31, 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 - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 11/26
12:00 pm-4:20 pm
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Wed 12/30
6:00 pm-12:20 am
1 stop6h 20m
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
Tue 12/29
6:00 pm-12:20 am
1 stop6h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$198
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Tue 12/15
7:00 am-12:24 pm
1 stop5h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 12/30
5:12 pm-12:02 am
1 stop6h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Tue 12/15
6:00 am-12:04 pm
1 stop6h 04m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 11/6
2:10 pm-11:00 pm
2 stops8h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$295
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Tue 12/8
11:10 am-5:10 pm
1 stop6h 00m
Chicago Midway
Thu 12/10
7:05 am-1:25 pm
1 stop6h 20m
$299
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 12/7
2:05 pm-10:45 pm
1 stop8h 40m
Chicago Midway
Thu 12/10
7:05 am-1:25 pm
1 stop6h 20m
$305
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Tue 12/8
11:32 am-2:21 pm
Nonstop2h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$306
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | 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 October is currently the most expensive (average of $543). 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.
What is the cheapest time of day to fly from VPS to CHI?
Find hourly flight availability from Valparaiso to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 31, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Valparaiso, Florida to Chicago as you normally would.
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 October 31, 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.
Crew
8.1
Boarding
7.7
Overall
7.3
Comfort
6.9
Entertainment
5.5
Food
5.9
Reviews
1 / 20
2.0
MediocreNic,Aug 2026
SRQ - ALB
Crew
8.1
Boarding
7.7
Overall
7.3
Comfort
6.9
Entertainment
5.5
Food
5.9
Reviews
1 / 20
2.0
MediocreNic,Aug 2026
SRQ - ALB
Crew
8.1
Boarding
7.7
Overall
7.3
Comfort
6.9
Entertainment
5.5
Food
5.9
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
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Valparaiso and Chicago flights
Browse other Valparaiso and Chicago flight options. Last updated on October 31, 2026.
Other flights from Valparaiso
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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 October 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$161 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$374 | Average$483 | FlexibilityNo cancel fee | On-time71% |