$50+ Cheap flights from Chicago (CHI) to Valparaiso, FL (VPS)
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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Jun 2 — Jun 91
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Valparaiso with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Valparaiso Destin-Ft Walton Beach are usually found in October or June, booked 12 days in advance, depart on a Monday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Valparaiso
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Best
Last-minute
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Cheapest flights from Chicago to ValparaisoExplore the most affordable flight options available from Chicago to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.
Explore the most affordable flight options available from Chicago to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Mon 6/156:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 5/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Mon 6/156:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/229:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Mon 6/296:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 5/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/179:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 7/206:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:44 pm
MDW
- VPS
Nonstop2h 11m
Allegiant Air
Fri 10/305:50 pm
VPS
- MDW
Nonstop2h 18m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Fri 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Thu 5/144:01 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$144
This Cheapflightsfares deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 8/106:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 7/319:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Fri 8/76:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Fri 6/126:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$158
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Mon 6/296:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:57 pm
ORD
- VPS
1 stop25h 41m
Multiple Airlines
Thu 8/2010:57 am
VPS
- ORD
1 stop9h 56m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$277
Best flights from Chicago to ValparaisoDiscover carefully curated flight deals from Chicago to Valparaiso that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 3, 2026.
Discover carefully curated flight deals from Chicago to Valparaiso that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 3, 2026.
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:55 pm
ORD
- VPS
1 stop7h 10m
Southwest
Wed 6/37:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Deal found 4/29![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:06 pm
ORD
- VPS
1 stop5h 07m
Delta
Sat 6/137:00 am
VPS
- ORD
1 stop5h 39m
Delta
Deal found 5/1![Delta logo]()
$375
This Sun Country Air deal was found by Cheapflights users on 5/3. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:19 pm
ORD
- VPS
1 stop20h 44m
Sun Country Air
Sun 6/146:03 pm
VPS
- ORD
1 stop23h 26m
Sun Country Air
Deal found 5/3![Sun Country Air logo]()
$384
This Delta deal was found by Cheapflights users on 4/30. 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 8/14:22 pm
MDW
- VPS
1 stop6h 41m
Delta
Sat 8/86:00 am
VPS
- MDW
1 stop4h 04m
Delta
Deal found 4/30![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:45 am
MDW
- VPS
2 stops9h 50m
Southwest
Thu 8/137:25 am
VPS
- MDW
1 stop6h 45m
Southwest
Deal found 4/28![Southwest logo]()
$400
This Sun Country Air deal was found by Cheapflights users on 4/28. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:25 pm
ORD
- VPS
1 stop22h 38m
Sun Country Air
Sun 6/76:03 pm
VPS
- ORD
1 stop24h 06m
Sun Country Air
Deal found 4/28![Sun Country Air logo]()
$416
This Delta deal was found by Cheapflights users on 4/30. 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.
Sun 5/2412:22 pm
ORD
- VPS
1 stop4h 18m
Delta
Fri 5/297:06 am
VPS
- ORD
1 stop6h 41m
Delta
Deal found 4/30![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 5/252:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Mon 6/17:20 am
VPS
- ORD
1 stop5h 30m
Southwest
Deal found 4/30![Southwest logo]()
$403
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:23 am
MDW
- VPS
1 stop6h 04m
Delta
Wed 5/276:00 am
VPS
- MDW
1 stop4h 00m
Delta
Deal found 4/29![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 5/197:00 am
MDW
- VPS
1 stop6h 10m
Southwest
Wed 5/272:00 pm
VPS
- MDW
1 stop5h 30m
Southwest
Deal found 4/30![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 5/3. 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.
Sun 5/246:23 am
MDW
- VPS
1 stop6h 04m
Delta
Fri 5/292:55 pm
VPS
- MDW
1 stop6h 14m
Delta
Deal found 5/3![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:10 am
MDW
- VPS
1 stop7h 45m
Southwest
Fri 10/3010:10 am
VPS
- MDW
1 stop6h 20m
Southwest
Deal found 4/28![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/11:39 pm
ORD
- VPS
1 stop5h 03m
Delta
Fri 8/75:06 pm
VPS
- ORD
1 stop5h 02m
Delta
Deal found 4/28![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:55 am
ORD
- VPS
2 stops9h 05m
Southwest
Wed 5/277:15 am
VPS
- ORD
2 stops11h 10m
Southwest
Deal found 4/29![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:41 pm
MDW
- VPS
1 stop6h 01m
Delta
Tue 8/112:40 pm
VPS
- MDW
1 stop7h 06m
Delta
Deal found 4/29![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:15 am
MDW
- VPS
1 stop6h 40m
Southwest
Sun 9/277:25 am
VPS
- MDW
2 stops6h 25m
Southwest
Deal found 4/28![Southwest logo]()
$419
This Delta deal was found by Cheapflights users on 5/3. 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.
Sat 8/810:56 am
MDW
- VPS
1 stop5h 05m
Delta
Sat 8/155:06 pm
VPS
- MDW
1 stop5h 30m
Delta
Deal found 5/3![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:10 am
MDW
- VPS
1 stop7h 05m
Southwest
Sat 5/303:05 pm
VPS
- MDW
1 stop5h 00m
Southwest
Deal found 5/1![Southwest logo]()
$422
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/252:59 pm
ORD
- VPS
1 stop5h 24m
Delta
Wed 5/271:17 pm
VPS
- ORD
1 stop5h 24m
Delta
Deal found 5/1![Delta logo]()
$408
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:24 am
ORD
- VPS
1 stop6h 42m
Delta
Mon 6/82:16 pm
VPS
- ORD
1 stop5h 15m
Delta
Deal found 5/2![Delta logo]()
$408
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:06 pm
ORD
- VPS
1 stop5h 07m
Delta
Thu 5/211:17 pm
VPS
- ORD
1 stop5h 18m
Delta
Deal found 4/29![Delta logo]()
$432
Last-minute flights from Chicago to ValparaisoDiscover last-minute flight deals from Chicago to Valparaiso. Data last updated May 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Valparaiso. Data last updated May 3, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:12 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Thu 5/74:01 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 4/29![Allegiant Air logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Thu 5/74:01 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Thu 5/144:01 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$144
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:08 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Sun 5/172:40 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:23 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Fri 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:37 pm
ORD
- VPS
1 stop25h 49m
Multiple Airlines
Sat 5/308:24 pm
VPS
- ORD
2 stops35h 31m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sat 5/239:37 pm
ORD
- VPS
1 stop25h 49m
Multiple Airlines
Fri 5/296:15 am
VPS
- ORD
2 stops13h 26m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Fri 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Mon 6/16:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Multiple Airlines
Sat 5/308:24 pm
VPS
- MDW
2 stops38h 45m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Multiple Airlines
Thu 5/286:40 pm
VPS
- MDW
2 stops27h 22m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Multiple Airlines
Mon 6/17:51 pm
VPS
- MDW
2 stops26h 11m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$227
One-way flights from Chicago to ValparaisoSearch for one-way flight options from Chicago to Valparaiso. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
Search for one-way flight options from Chicago to Valparaiso. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/299:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$50
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Mon 6/229:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$56
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Deal found 4/29![Allegiant Air logo]()
$61
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/229:23 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:37 pm
ORD
- VPS
1 stop25h 49m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:37 pm
ORD
- VPS
1 stop25h 49m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 5/288:05 am
ORD
- VPS
2 stops39h 08m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:50 pm
ORD
- VPS
2 stops32h 29m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sat 5/3011:59 am
MDW
- VPS
2 stops34h 20m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Mon 5/256:00 am
MDW
- VPS
2 stops35h 05m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sun 5/175:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$180
Find flight deals from Chicago to Valparaiso
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Valparaiso (VPS). 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 May 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $98 (Cheapflightsfares) |
One-way from | $50 (Kiwi.com) |
Popular in | September |
Cheapest in | October |
Average price | $348 |
Good round-trip deal | $138 or less |
Good one-way deal | $89 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Valparaiso 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 May 3, 2026.
Use the filters below to find and compare flights from Chicago to Valparaiso that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sat 5/30
1:55 pm-9:05 pm
1 stop7h 10m
Valparaiso Destin-Ft Walton Beach
Wed 6/3
7:15 am-12:50 pm
1 stop5h 35m
$374
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sat 6/6
6:06 pm-11:13 pm
1 stop5h 07m
Valparaiso Destin-Ft Walton Beach
Sat 6/13
7:00 am-12:39 pm
1 stop5h 39m
$375
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Sat 8/1
4:22 pm-11:03 pm
1 stop6h 41m
Valparaiso Destin-Ft Walton Beach
Sat 8/8
6:00 am-10:04 am
1 stop4h 04m
$375
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Thu 6/11
8:19 pm-5:03 pm
1 stop20h 44m
Valparaiso Destin-Ft Walton Beach
Sun 6/14
6:03 pm-5:29 pm
1 stop23h 26m
$384
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sun 5/24
12:22 pm-4:40 pm
1 stop4h 18m
Valparaiso Destin-Ft Walton Beach
Fri 5/29
7:06 am-1:47 pm
1 stop6h 41m
$393
Quickest round-trip
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Wed 5/20
6:23 am-12:27 pm
1 stop6h 04m
Valparaiso Destin-Ft Walton Beach
Wed 5/27
6:00 am-10:00 am
1 stop4h 00m
$393
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Sun 5/24
6:23 am-12:27 pm
1 stop6h 04m
Valparaiso Destin-Ft Walton Beach
Fri 5/29
2:55 pm-9:09 pm
1 stop6h 14m
$393
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sat 8/1
1:39 pm-6:42 pm
1 stop5h 03m
Valparaiso Destin-Ft Walton Beach
Fri 8/7
5:06 pm-10:08 pm
1 stop5h 02m
$394
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Fri 8/7
12:41 pm-6:42 pm
1 stop6h 01m
Valparaiso Destin-Ft Walton Beach
Tue 8/11
2:40 pm-9:46 pm
1 stop7h 06m
$394
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Sat 8/8
10:56 am-4:01 pm
1 stop5h 05m
Valparaiso Destin-Ft Walton Beach
Sat 8/15
5:06 pm-10:36 pm
1 stop5h 30m
$395
Showing 1-10 of 39 resultsSorted by cheapest first
Compare providers for flights from Chicago to Valparaiso
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 Chicago to Valparaiso in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Valparaiso, Florida flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Valparaiso, Florida flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Valparaiso, Florida flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Valparaiso, Florida 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 Chicago-Valparaiso, Florida 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 Chicago to Valparaiso
Have a flexible travel schedule? Discover the best time to fly to Valparaiso from Chicago with our price prediction graph.
CHI-VPS
MDW-VPS
ORD-VPS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Valparaiso
CHI-VPS
MDW-VPS
ORD-VPS
How far ahead should I book a flight from Chicago to Valparaiso, Florida?
Booking 10 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Valparaiso, Florida. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Valparaiso, Florida?
Currently, October is the cheapest month in which you can book a flight from Chicago to Valparaiso, Florida (average of $52). Flying from Chicago to Valparaiso, Florida in January is currently the most expensive (average of $250). 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 CHI to VPS?
Find hourly flight availability from Chicago to Valparaiso. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 3, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Valparaiso, Florida in the afternoon. If you’re flexible enough to do this you can expect to save up to 54% on your trip compared to booking a flight at noon.
Weekly flight availability from Chicago to Valparaiso, Florida
Explore weekly flight availability from Chicago to Valparaiso. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 3, 2026.
The most flights from CHI to VPS are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chicago to Valparaiso, Florida?
Reviews of airlines servicing Valparaiso
Get insights into the airlines that provide service to Valparaiso. 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 Valparaiso. Reviews last updated May 3, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAllegiant Air from Chicago to Valparaiso by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Valparaiso. 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 Valparaiso?
Book flights to Valparaiso if you plan to visit one of these locationsCrestview
Andalusia
Niceville
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Chicago and Valparaiso flights
Browse other Chicago and Valparaiso flight options. Last updated on May 3, 2026.
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Explore flights to Valparaiso departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 3, 2026.
Top 4 airlines flying from Chicago to Valparaiso
Discover the top 4 airlines that operate flights from Chicago to Valparaiso. 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 2,558,603 searches. Data last updated May 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$216 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$212 | Average$413 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$235 | Average$406 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$474 | FlexibilityNo cancel fee | On-timeN/A |