$68+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Aug 29 — Sep 51
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 April, booked 21 days in advance, depart on a Monday or Sunday and return on a Thursday
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 July 30, 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 July 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:15 pm
MDW
- VPS
Nonstop2h 11m
Allegiant Air
Thu 11/196:30 am
VPS
- MDW
Nonstop2h 24m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$78
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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
Thu 11/196:30 am
VPS
- MDW
Nonstop2h 24m
Allegiant Air
Deal found 7/28![Allegiant Air logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:38 am
MDW
- VPS
Nonstop2h 11m
Allegiant Air
Mon 11/910:00 am
VPS
- MDW
Nonstop2h 18m
Allegiant Air
Deal found 7/27![Allegiant Air logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:25 pm
MDW
- VPS
Nonstop2h 11m
Allegiant Air
Fri 10/166:12 pm
VPS
- MDW
Nonstop2h 18m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$164
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
Fri 8/149:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 8/176:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 7/29![Allegiant Air logo]()
$182
This Trip.com deal was found by Cheapflights users on 7/27. 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 Trip.com 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 7/27![Allegiant Air logo]()
$228
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.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 7/27![Allegiant Air logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/2911:06 am
ORD
- VPS
1 stop12h 31m
Multiple Airlines
Sun 11/17:00 am
VPS
- ORD
1 stop27h 01m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 10/206:20 am
ORD
- VPS
2 stops16h 59m
Delta
Wed 10/282:07 pm
VPS
- ORD
1 stop18h 46m
Delta
Deal found 7/29![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Sat 9/52:41 pm
ORD
- VPS
1 stop25h 39m
Multiple Airlines
Fri 9/1111:43 am
VPS
- ORD
2 stops27h 37m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Wed 8/262:41 pm
ORD
- VPS
1 stop25h 38m
Multiple Airlines
Wed 9/24:40 pm
VPS
- ORD
2 stops27h 24m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$338
This Sun Country Air deal was found by Cheapflights users on 7/26. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:30 am
ORD
- VPS
1 stop8h 34m
Sun Country Air
Sun 8/306:09 pm
VPS
- ORD
1 stop15h 34m
Sun Country Air
Deal found 7/26![Sun Country Air logo]()
$344
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 July 30, 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 July 30, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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 8/245:30 pm
MDW
- VPS
1 stop3h 30m
Southwest
Thu 8/2712:40 pm
VPS
- MDW
1 stop6h 40m
Southwest
Deal found 7/28![Southwest logo]()
$317
This Sun Country Air deal was found by Cheapflights users on 7/26. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:30 am
ORD
- VPS
1 stop8h 34m
Sun Country Air
Sun 8/306:09 pm
VPS
- ORD
1 stop15h 34m
Sun Country Air
Deal found 7/26![Sun Country Air logo]()
$344
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:30 am
ORD
- VPS
1 stop5h 25m
Delta
Wed 10/75:07 pm
VPS
- ORD
1 stop6h 45m
Delta
Deal found 7/25![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 7/27. 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.
Wed 9/165:20 pm
MDW
- VPS
1 stop3h 45m
Southwest
Tue 9/222:15 pm
VPS
- MDW
1 stop6h 35m
Southwest
Deal found 7/27![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 7/26. 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 9/92:40 pm
MDW
- VPS
1 stop6h 25m
Southwest
Wed 9/167:15 am
VPS
- MDW
2 stops8h 10m
Southwest
Deal found 7/26![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/27. 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.
Wed 9/1611:10 am
MDW
- VPS
2 stops9h 55m
Southwest
Mon 9/2112:40 pm
VPS
- MDW
1 stop6h 40m
Southwest
Deal found 7/27![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 7/26. 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.
Wed 9/910:44 am
ORD
- VPS
1 stop5h 16m
Delta
Wed 9/162:48 pm
VPS
- ORD
1 stop6h 08m
Delta
Deal found 7/26![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 7/29. 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 8/262:00 pm
MDW
- VPS
2 stops7h 05m
Southwest
Wed 9/212:05 pm
VPS
- MDW
2 stops7h 20m
Southwest
Deal found 7/29![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 7/27. 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.
Mon 9/146:25 pm
ORD
- VPS
1 stop14h 09m
Delta
Mon 9/216:00 am
VPS
- ORD
1 stop14h 56m
Delta
Deal found 7/27![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sat 9/56:45 am
MDW
- VPS
2 stops9h 50m
Southwest
Fri 9/116:25 pm
VPS
- MDW
1 stop4h 00m
Southwest
Deal found 7/27![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 7/29. 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 11/186:00 am
MDW
- VPS
1 stop10h 01m
Delta
Wed 11/255:00 pm
VPS
- MDW
1 stop5h 56m
Delta
Deal found 7/29![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 7/29. 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 11/185:30 am
ORD
- VPS
1 stop13h 13m
Delta
Wed 11/2512:08 pm
VPS
- ORD
1 stop6h 54m
Delta
Deal found 7/29![Delta logo]()
$420
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/1011:25 am
MDW
- VPS
1 stop5h 50m
Southwest
Sat 10/174:55 pm
VPS
- MDW
1 stop5h 20m
Southwest
Deal found 7/25![Southwest logo]()
$363
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 10/2010:44 am
ORD
- VPS
1 stop7h 58m
Delta
Sat 10/2411:45 am
VPS
- ORD
1 stop5h 18m
Delta
Deal found 7/29![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 7/27. 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.
Sun 9/135:30 am
ORD
- VPS
1 stop15h 25m
Delta
Tue 9/227:00 am
VPS
- ORD
1 stop9h 37m
Delta
Deal found 7/27![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 11/1810:32 am
ORD
- VPS
1 stop5h 29m
Delta
Sun 11/229:30 am
VPS
- ORD
1 stop5h 08m
Delta
Deal found 7/25![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/86:13 pm
ORD
- VPS
1 stop5h 06m
Delta
Tue 10/135:07 pm
VPS
- ORD
1 stop6h 45m
Delta
Deal found 7/25![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 7/29. 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 10/218:05 am
ORD
- VPS
1 stop5h 56m
Delta
Fri 10/237:20 pm
VPS
- ORD
2 stops13h 33m
Delta
Deal found 7/29![Delta logo]()
$451
This Delta deal was found by Cheapflights users on 7/27. 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.
Thu 9/38:24 pm
ORD
- VPS
1 stop16h 49m
Delta
Mon 9/76:00 am
VPS
- ORD
1 stop4h 13m
Delta
Deal found 7/27![Delta logo]()
$453
Last-minute flights from Chicago to ValparaisoDiscover last-minute flight deals from Chicago to Valparaiso. Data last updated July 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Valparaiso. Data last updated July 30, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.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 7/27![Allegiant Air logo]()
$237
This Trip.com deal was found by Cheapflights users on 7/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:20 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 8/106:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 7/27![Allegiant Air logo]()
$273
This Trip.com deal was found by Cheapflights users on 7/27. 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 Trip.com 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 7/27![Allegiant Air logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 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
Fri 8/146:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$278
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Fri 8/146:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$254
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
Fri 8/149:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 8/176:14 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 7/29![Allegiant Air logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:25 pm
MDW
- VPS
Nonstop2h 14m
Multiple Airlines
Mon 8/179:07 pm
VPS
- MDW
2 stops37h 48m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/149:25 pm
MDW
- VPS
Nonstop2h 14m
Multiple Airlines
Sun 8/305:09 pm
VPS
- MDW
3 stops29h 38m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$300
This Sun Country Air deal was found by Cheapflights users on 7/26. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:30 am
ORD
- VPS
1 stop8h 34m
Sun Country Air
Sun 8/306:09 pm
VPS
- ORD
1 stop15h 34m
Sun Country Air
Deal found 7/26![Sun Country Air logo]()
$344
This Southwest deal was found by Cheapflights users on 7/28. 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 8/245:30 pm
MDW
- VPS
1 stop3h 30m
Southwest
Thu 8/2712:40 pm
VPS
- MDW
1 stop6h 40m
Southwest
Deal found 7/28![Southwest logo]()
$317
This American Airlines deal was found by Cheapflights users on 7/26. 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 8/258:25 am
ORD
- VPS
Nonstop2h 28m
American Airlines
Tue 9/111:28 am
VPS
- ORD
Nonstop2h 45m
American Airlines
Deal found 7/26![American Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Wed 8/262:41 pm
ORD
- VPS
1 stop25h 38m
Multiple Airlines
Wed 9/24:40 pm
VPS
- ORD
2 stops27h 24m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$338
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 July 30, 2026.
Search for one-way flight options from Chicago to Valparaiso. Find affordable one-way fares based on user searches. Data last updated July 30, 2026.
This Kissandfly.com deal was found by Cheapflights users on 7/27. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:24 pm
MDW
- VPS
Nonstop2h 11m
Allegiant Air
Deal found 7/27![Allegiant Air logo]()
$68
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 10/2911:06 am
ORD
- VPS
1 stop12h 31m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Sat 8/292:41 pm
ORD
- VPS
1 stop25h 38m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/282:46 pm
ORD
- VPS
2 stops32h 51m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Sat 8/222:41 pm
ORD
- VPS
1 stop25h 38m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sun 8/307:05 am
ORD
- VPS
2 stops34h 08m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/262:41 pm
ORD
- VPS
1 stop25h 38m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Wed 9/307:11 am
ORD
- VPS
3 stops40h 08m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$155
This Southwest deal was found by Cheapflights users on 7/28. 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 8/299:05 am
MDW
- VPS
1 stop5h 15m
Southwest
Deal found 7/28![Southwest logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:20 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 7/25![Allegiant Air logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:45 am
MDW
- VPS
2 stops44h 03m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$167
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 July 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $78 (Cheapflightsfares) |
One-way from | $68 (Kissandfly.com) |
Popular in | August |
Cheapest in | October |
Average price | $403 |
Good round-trip deal | $118 or less |
Good one-way deal | $90 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 July 30, 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
Quickest round-trip
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Mon 8/24
5:30 pm-9:00 pm
1 stop3h 30m
Valparaiso Destin-Ft Walton Beach
Thu 8/27
12:40 pm-7:20 pm
1 stop6h 40m
$317
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Wed 9/16
5:20 pm-9:05 pm
1 stop3h 45m
Valparaiso Destin-Ft Walton Beach
Tue 9/22
2:15 pm-8:50 pm
1 stop6h 35m
$321
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Wed 9/9
2:40 pm-9:05 pm
1 stop6h 25m
Valparaiso Destin-Ft Walton Beach
Wed 9/16
7:15 am-3:25 pm
2 stops8h 10m
$327
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Wed 9/16
11:10 am-9:05 pm
2 stops9h 55m
Valparaiso Destin-Ft Walton Beach
Mon 9/21
12:40 pm-7:20 pm
1 stop6h 40m
$327
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Wed 8/26
2:00 pm-9:05 pm
2 stops7h 05m
Valparaiso Destin-Ft Walton Beach
Wed 9/2
12:05 pm-7:25 pm
2 stops7h 20m
$332
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Sat 9/5
6:45 am-4:35 pm
2 stops9h 50m
Valparaiso Destin-Ft Walton Beach
Fri 9/11
6:25 pm-10:25 pm
1 stop4h 00m
$332
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sun 8/23
8:30 am-5:04 pm
1 stop8h 34m
Valparaiso Destin-Ft Walton Beach
Sun 8/30
6:09 pm-9:43 am
1 stop15h 34m
$344
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Sat 10/10
11:25 am-5:15 pm
1 stop5h 50m
Valparaiso Destin-Ft Walton Beach
Sat 10/17
4:55 pm-10:15 pm
1 stop5h 20m
$363
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sat 10/3
5:30 am-10:55 am
1 stop5h 25m
Valparaiso Destin-Ft Walton Beach
Wed 10/7
5:07 pm-11:52 pm
1 stop6h 45m
$405
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Wed 9/9
10:44 am-4:00 pm
1 stop5h 16m
Valparaiso Destin-Ft Walton Beach
Wed 9/16
2:48 pm-8:56 pm
1 stop6h 08m
$405
Showing 1-10 of 37 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 July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
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 $235). Flying from Chicago to Valparaiso, Florida in May is currently the most expensive (average of $499). 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 July 30, 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 53% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Chicago to Valparaiso, Florida?
Airfare is below average for this route at the moment.
Chicago to Valparaiso, Florida flights typically cost between $383 and $509 in October.The cheapest round-trip price found within the last 5 days was $78 on Allegiant Air (Oct 23-Nov 19).
How far ahead should I book a flight from Chicago to Valparaiso, Florida?
Booking 83 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.
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 July 30, 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.
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
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 locationsAndalusia
Niceville
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Chicago and Valparaiso flights
Browse other Chicago and Valparaiso flight options. Last updated on July 30, 2026.
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Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on July 30, 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 July 30, 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 July 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$357 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$250 | Average$413 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$295 | Average$437 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$334 | Average$474 | FlexibilityNo cancel fee | On-timeN/A |