$54+ Cheap flights from Chicago (CHI) to Valparaiso, FL (VPS)
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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Nov 29 — Dec 61
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 55 days in advance, depart on a Monday or Sunday and return on a Friday
Cheap flight deals from Chicago to Valparaiso
Cheapest
Best
Last-minute
One-way
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 October 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 October 30, 2026.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:08 pm -
Nonstop2h 11m
Thu 11/196:30 am -
Nonstop2h 24m
Deal found 10/29![Allegiant Air logo]()
$84
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:44 pm -
Nonstop2h 11m
Fri 11/67:30 am -
Nonstop2h 18m
Deal found 10/27![Allegiant Air logo]()
$152
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:08 pm -
Nonstop2h 11m
Mon 11/1610:00 am -
Nonstop2h 18m
Deal found 10/29![Allegiant Air logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/166:00 am -
1 stop13h 06m
Thu 11/198:47 am -
2 stops15h 26m
Deal found 10/25![Multiple Airlines logo]()
$315
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.
Sat 11/74:00 pm -
2 stops27h 21m
Fri 11/207:00 am -
1 stop8h 57m
Deal found 10/29![Multiple Airlines logo]()
$397
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.
Tue 12/155:24 pm -
2 stops44h 23m
Thu 12/246:10 pm -
1 stop16h 13m
Deal found 10/29![Multiple Airlines logo]()
$405
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 12/86:00 am -
1 stop9h 50m
Thu 12/1012:07 pm -
1 stop11h 52m
Deal found 10/28![American Airlines logo]()
$439
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 October 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 October 30, 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.
Thu 12/174:00 pm -
1 stop5h 00m
Tue 12/226:00 pm -
1 stop6h 20m
Deal found 10/27![Southwest logo]()
$330
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/165:25 pm -
1 stop5h 42m
Tue 3/25:05 pm -
1 stop5h 05m
Deal found 10/29![Delta logo]()
$465
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 2/45:30 am -
1 stop8h 05m
Mon 2/811:00 am -
1 stop7h 00m
Deal found 10/26![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 10/25. 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.
Fri 12/411:30 am -
2 stops9h 45m
Sun 12/62:10 pm -
1 stop10h 00m
Deal found 10/25![Southwest logo]()
$381
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/167:10 am -
1 stop4h 03m
Tue 3/29:25 am -
1 stop7h 12m
Deal found 10/29![Delta logo]()
$465
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/911:20 am -
1 stop5h 00m
Sun 1/311:00 pm -
1 stop5h 47m
Deal found 10/29![Delta logo]()
$494
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/26:20 am -
1 stop5h 00m
Sat 4/1010:05 am -
1 stop5h 45m
Deal found 10/29![Southwest logo]()
$491
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:27 am -
1 stop6h 31m
Tue 12/16:00 am -
1 stop6h 04m
Deal found 10/29![Delta logo]()
$523
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/25:25 pm -
1 stop5h 42m
Fri 4/97:45 am -
1 stop4h 11m
Deal found 10/28![Delta logo]()
$523
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.
Fri 3/265:15 am -
1 stop6h 35m
Fri 4/24:00 pm -
2 stops9h 05m
Deal found 10/26![Southwest logo]()
$531
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/25:30 am -
1 stop5h 43m
Fri 4/95:05 pm -
1 stop6h 45m
Deal found 10/28![Delta logo]()
$523
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.
Thu 4/19:00 am -
1 stop6h 15m
Sun 4/412:00 pm -
1 stop9h 05m
Deal found 10/27![Southwest logo]()
$531
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.
Thu 4/15:55 pm -
1 stop5h 12m
Sun 4/47:05 pm -
1 stop4h 45m
Deal found 10/27![Delta logo]()
$550
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.
Thu 11/198:04 am -
1 stop5h 55m
Sun 11/225:05 pm -
1 stop6h 49m
Deal found 10/26![Delta logo]()
$581
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:49 am -
1 stop7h 10m
Mon 11/306:00 am -
1 stop4h 25m
Deal found 10/29![Delta logo]()
$594
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/262:00 pm -
1 stop7h 28m
Mon 11/306:00 am -
1 stop4h 25m
Deal found 10/29![Delta logo]()
$619
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.
Thu 2/47:00 am -
2 stops11h 27m
Mon 2/83:00 pm -
1 stop5h 30m
Deal found 10/26![Delta logo]()
$716
Last-minute flights from Chicago to ValparaisoDiscover last-minute flight deals from Chicago to Valparaiso. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Valparaiso. Data last updated October 30, 2026 and is based on user searches.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:44 pm -
Nonstop2h 11m
Fri 11/67:30 am -
Nonstop2h 18m
Deal found 10/27![Allegiant Air logo]()
$152
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.
Sat 11/74:00 pm -
2 stops27h 21m
Fri 11/207:00 am -
1 stop8h 57m
Deal found 10/29![Multiple Airlines logo]()
$397
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:08 pm -
Nonstop2h 11m
Mon 11/1610:00 am -
Nonstop2h 18m
Deal found 10/29![Allegiant Air logo]()
$165
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:08 pm -
Nonstop2h 11m
Thu 11/196:30 am -
Nonstop2h 24m
Deal found 10/29![Allegiant Air logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/166:00 am -
1 stop13h 06m
Thu 11/198:47 am -
2 stops15h 26m
Deal found 10/25![Multiple Airlines logo]()
$315
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.
Sat 11/218:05 am -
1 stop14h 13m
Mon 11/2312:10 pm -
1 stop12h 10m
Deal found 10/29![American Airlines logo]()
$473
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:49 am -
1 stop7h 10m
Tue 12/12:46 pm -
1 stop6h 07m
Deal found 10/29![Delta logo]()
$498
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 October 30, 2026.
Search for one-way flight options from Chicago to Valparaiso. Find affordable one-way fares based on user searches. Data last updated October 30, 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.
Mon 11/161:08 pm -
Nonstop2h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Allegiant Air logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sun 1/39:41 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Allegiant Air logo]()
$68
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:38 am -
Nonstop2h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Allegiant Air logo]()
$105
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/84:00 pm -
2 stops39h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$144
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:54 am -
1 stop7h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Sun Country Air logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Thu 11/1910:19 am -
2 stops25h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$181
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.
Fri 1/15:25 pm -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$182
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.
Sat 11/218:28 am -
2 stops28h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$191
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.
Sat 11/217:49 am -
2 stops29h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$208
This CheapOair deal was found by Cheapflights users on 10/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:51 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Allegiant Air logo]()
$226
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 12/89:06 pm -
1 stop14h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$226
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/26:00 am -
1 stop5h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$234
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $84 (CheapOair) |
One-way from | $54 (Jetabroad) |
Popular in | November |
Cheapest in | October |
Average price | $189 |
Good round-trip deal | $155 or less |
Good one-way deal | $53 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 7,457,451 searches. Data last updated October 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
ChicagoValparaiso
ORD Chicago O'Hare Intl - VPS Valparaiso Destin-Ft Walton Beach
ORDVPS
Chicago O'Hare Intl
Thu 11/19
10:19 am-12:18 pm
2 stops25h 59m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$181
ChicagoValparaiso
ORD Chicago O'Hare Intl - VPS Valparaiso Destin-Ft Walton Beach
ORDVPS
Chicago O'Hare Intl
Wed 11/25
9:54 am-5:26 pm
1 stop7h 32m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$181
ChicagoValparaiso
MDW Chicago Midway - VPS Valparaiso Destin-Ft Walton Beach
MDWVPS
Chicago Midway
Fri 1/1
11:30 am-9:15 pm
2 stops9h 45m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$187
ChicagoValparaiso
ORD Chicago O'Hare Intl - VPS Valparaiso Destin-Ft Walton Beach
ORDVPS
Chicago O'Hare Intl
Sat 11/21
7:49 am-12:59 pm
2 stops29h 10m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
ChicagoValparaiso
MDW Chicago Midway - VPS Valparaiso Destin-Ft Walton Beach
MDWVPS
Chicago Midway
Sat 1/2
6:00 am-11:24 am
1 stop5h 24m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoValparaiso
ORD Chicago O'Hare Intl - VPS Valparaiso Destin-Ft Walton Beach
ORDVPS
Chicago O'Hare Intl
Sat 1/2
5:25 am-11:24 am
1 stop5h 59m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoValparaiso
ORD Chicago O'Hare Intl - VPS Valparaiso Destin-Ft Walton Beach
ORDVPS
Chicago O'Hare Intl
Sun 4/4
6:49 am-12:22 pm
1 stop5h 33m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$263
ChicagoValparaiso
MDW Chicago Midway - VPS Valparaiso Destin-Ft Walton Beach
MDWVPS
Chicago Midway
Sat 2/13
5:25 pm-11:07 pm
1 stop5h 42m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$263
ChicagoValparaiso
ORD Chicago O'Hare Intl - VPS Valparaiso Destin-Ft Walton Beach
ORDVPS
Chicago O'Hare Intl
Fri 1/1
7:25 am-2:18 pm
1 stop6h 53m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$263
ChicagoValparaiso
MDW Chicago Midway - VPS Valparaiso Destin-Ft Walton Beach
MDWVPS
Chicago Midway
Sat 1/2
7:20 am-1:45 pm
1 stop6h 25m
Valparaiso Destin-Ft Walton Beach
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
Showing 1-10 of 33 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 October.
| 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
ORD-VPS
MDW-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
ORD-VPS
MDW-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 $241). Flying from Chicago to Valparaiso, Florida in May is currently the most expensive (average of $517). 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 October 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 54% 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 $288 and $677 in November.The cheapest round-trip price found within the last 5 days was $84 on Allegiant Air (Nov 16-Nov 19).
How far ahead should I book a flight from Chicago to Valparaiso, Florida?
Booking 41 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 October 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.
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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
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Chicago and Valparaiso flights
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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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$129 | Average$419 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$250 | Average$434 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$295 | Average$438 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$334 | Average$497 | FlexibilityNo cancel fee | On-timeN/A |