$54+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VPS
Jul 18 — Jul 251
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 12 days in advance, depart on a Monday or Thursday 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 June 18, 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 June 18, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 8/36:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 7/276:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 6/14![Allegiant Air logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/139:20 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 7/206:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/15![Allegiant Air logo]()
$149
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Fri 7/36:05 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$159
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/139:20 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Fri 7/176:11 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 6/15![Allegiant Air logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/1610:40 pm
ORD
- VPS
1 stop17h 40m
Multiple Airlines
Sun 9/2011:06 am
VPS
- ORD
1 stop22h 55m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$315
This Sun Country Air deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/206:32 pm
ORD
- VPS
1 stop22h 27m
Sun Country Air
Sun 8/236:09 pm
VPS
- ORD
1 stop15h 02m
Sun Country Air
Deal found 6/17![Sun Country Air logo]()
$334
This Sun Country Air deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/237:25 am
ORD
- VPS
1 stop9h 38m
Sun Country Air
Sun 7/266:08 pm
VPS
- ORD
1 stop23h 16m
Sun Country Air
Deal found 6/16![Sun Country Air logo]()
$344
This CheapOair deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/248:10 pm
ORD
- VPS
1 stop18h 56m
JetBlue
Mon 7/273:59 pm
VPS
- ORD
1 stop18h 07m
JetBlue
Deal found 6/17![JetBlue logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/1610:40 pm
ORD
- VPS
1 stop17h 40m
Multiple Airlines
Fri 9/255:53 pm
VPS
- ORD
2 stops25h 51m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$362
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 June 18, 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 June 18, 2026.
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/31:46 pm
ORD
- VPS
1 stop4h 59m
Delta
Tue 7/72:45 pm
VPS
- ORD
1 stop5h 48m
Delta
Deal found 6/15![Delta logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Multiple Airlines
Mon 7/279:06 pm
VPS
- MDW
3 stops19h 45m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 8/37:00 am
MDW
- VPS
1 stop6h 20m
Southwest
Wed 8/52:15 pm
VPS
- MDW
1 stop6h 30m
Southwest
Deal found 6/13![Southwest logo]()
$403
This Sun Country Air deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/26:31 pm
ORD
- VPS
1 stop22h 32m
Sun Country Air
Thu 8/66:03 pm
VPS
- ORD
1 stop23h 21m
Sun Country Air
Deal found 6/14![Sun Country Air logo]()
$434
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/85:06 pm
VPS
- MDW
1 stop5h 30m
Delta
Deal found 6/16![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/242:45 pm
MDW
- VPS
1 stop4h 30m
Southwest
Mon 7/272:00 pm
VPS
- MDW
1 stop6h 05m
Southwest
Deal found 6/17![Southwest logo]()
$453
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/79:54 am
ORD
- VPS
1 stop6h 07m
Delta
Tue 8/112:45 pm
VPS
- ORD
1 stop6h 10m
Delta
Deal found 6/17![Delta logo]()
$413
This Sun Country Air deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/267:30 am
ORD
- VPS
1 stop9h 38m
Sun Country Air
Thu 7/306:03 pm
VPS
- ORD
1 stop25h 21m
Sun Country Air
Deal found 6/16![Sun Country Air logo]()
$464
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/710:54 am
MDW
- VPS
1 stop5h 07m
Delta
Wed 8/1212:00 pm
VPS
- MDW
1 stop4h 15m
Delta
Deal found 6/15![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/146:05 am
MDW
- VPS
1 stop5h 10m
Delta
Tue 8/1812:00 pm
VPS
- MDW
1 stop4h 15m
Delta
Deal found 6/14![Delta logo]()
$413
This Sun Country Air deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/26:31 pm
ORD
- VPS
1 stop22h 32m
Sun Country Air
Sun 8/96:05 pm
VPS
- ORD
1 stop23h 34m
Sun Country Air
Deal found 6/16![Sun Country Air logo]()
$544
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/95:30 am
ORD
- VPS
1 stop5h 45m
Delta
Wed 8/129:21 am
VPS
- ORD
1 stop4h 48m
Delta
Deal found 6/17![Delta logo]()
$422
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/96:05 am
MDW
- VPS
1 stop5h 10m
Delta
Wed 8/126:00 am
VPS
- MDW
1 stop3h 59m
Delta
Deal found 6/17![Delta logo]()
$422
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/81:44 pm
ORD
- VPS
1 stop4h 58m
Delta
Sat 7/1111:14 am
VPS
- ORD
1 stop5h 58m
Delta
Deal found 6/17![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/91:44 pm
ORD
- VPS
1 stop7h 05m
Delta
Mon 7/135:06 pm
VPS
- ORD
1 stop6h 47m
Delta
Deal found 6/15![Delta logo]()
$499
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/25:30 am
ORD
- VPS
1 stop4h 59m
Delta
Wed 7/85:06 pm
VPS
- ORD
1 stop6h 47m
Delta
Deal found 6/15![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/139:30 am
ORD
- VPS
1 stop6h 30m
Delta
Sat 9/192:11 pm
VPS
- ORD
1 stop7h 17m
Delta
Deal found 6/18![Delta logo]()
$856
Last-minute flights from Chicago to ValparaisoDiscover last-minute flight deals from Chicago to Valparaiso. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Valparaiso. Data last updated June 18, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 6/15![Allegiant Air logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Fri 7/36:05 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/139:20 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 7/206:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/15![Allegiant Air logo]()
$149
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/139:20 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Fri 7/176:11 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$168
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
Wed 7/158:29 am
ORD
- VPS
Nonstop2h 32m
American Airlines
Wed 7/2211:32 am
VPS
- ORD
Nonstop2h 42m
American Airlines
Deal found 6/15![American Airlines logo]()
$376
This Sun Country Air deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/237:25 am
ORD
- VPS
1 stop9h 38m
Sun Country Air
Sun 7/266:08 pm
VPS
- ORD
1 stop23h 16m
Sun Country Air
Deal found 6/16![Sun Country Air logo]()
$344
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Thu 7/237:25 am
ORD
- VPS
1 stop9h 38m
Multiple Airlines
Sun 7/263:59 pm
VPS
- ORD
2 stops16h 51m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$369
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 8/36:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Mon 7/276:10 pm
VPS
- MDW
Nonstop2h 20m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$101
This CheapOair deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/248:10 pm
ORD
- VPS
1 stop18h 56m
JetBlue
Mon 7/273:59 pm
VPS
- ORD
1 stop18h 07m
JetBlue
Deal found 6/17![JetBlue logo]()
$349
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/295:30 am
ORD
- VPS
1 stop6h 59m
Delta
Wed 8/52:45 pm
VPS
- ORD
1 stop6h 10m
Delta
Deal found 6/14![Delta logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 6/16![Allegiant Air logo]()
$180
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 June 18, 2026.
Search for one-way flight options from Chicago to Valparaiso. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/249:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/14![Allegiant Air logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 6/269:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$58
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/79:25 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$64
This Trip.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/39:15 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/15![Allegiant Air logo]()
$71
This Trip.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 6/229:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 6/13![Allegiant Air logo]()
$79
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/109:21 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/69:20 pm
MDW
- VPS
Nonstop2h 14m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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
Deal found 6/16![Multiple Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/1211:06 am
ORD
- VPS
1 stop29h 14m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/138:05 am
ORD
- VPS
2 stops15h 12m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/88:05 am
ORD
- VPS
2 stops35h 35m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/159:57 pm
ORD
- VPS
1 stop19h 08m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$145
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 June 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $96 (Cheapflightsfares) |
One-way from | $54 (Kiwi.com) |
Popular in | June |
Cheapest in | October |
Average price | $453 |
Good round-trip deal | $188 or less |
Good one-way deal | $50 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 June 18, 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
Fri 7/3
1:46 pm-6:45 pm
1 stop4h 59m
Valparaiso Destin-Ft Walton Beach
Tue 7/7
2:45 pm-8:33 pm
1 stop5h 48m
$393
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
5:06 pm-10:36 pm
1 stop5h 30m
$395
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Fri 7/24
9:21 pm-11:35 pm
Nonstop2h 14m
Valparaiso Destin-Ft Walton Beach
Mon 7/27
9:06 pm-4:51 pm
3 stops19h 45m
$396
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Mon 8/3
7:00 am-1:20 pm
1 stop6h 20m
Valparaiso Destin-Ft Walton Beach
Wed 8/5
2:15 pm-8:45 pm
1 stop6h 30m
$403
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Fri 8/7
9:54 am-4:01 pm
1 stop6h 07m
Valparaiso Destin-Ft Walton Beach
Tue 8/11
2:45 pm-8:55 pm
1 stop6h 10m
$413
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Fri 8/7
10:54 am-4:01 pm
1 stop5h 07m
Valparaiso Destin-Ft Walton Beach
Wed 8/12
12:00 pm-4:15 pm
1 stop4h 15m
$413
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Fri 8/14
6:05 am-11:15 am
1 stop5h 10m
Valparaiso Destin-Ft Walton Beach
Tue 8/18
12:00 pm-4:15 pm
1 stop4h 15m
$413
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sun 8/9
5:30 am-11:15 am
1 stop5h 45m
Valparaiso Destin-Ft Walton Beach
Wed 8/12
9:21 am-2:09 pm
1 stop4h 48m
$422
Quickest round-trip
ChicagoValparaiso
MDW - VPS
MDWVPS
Chicago Midway
Sun 8/9
6:05 am-11:15 am
1 stop5h 10m
Valparaiso Destin-Ft Walton Beach
Wed 8/12
6:00 am-9:59 am
1 stop3h 59m
$422
ChicagoValparaiso
ORD - VPS
ORDVPS
Chicago O'Hare Intl
Sun 8/2
6:31 pm-5:03 pm
1 stop22h 32m
Valparaiso Destin-Ft Walton Beach
Thu 8/6
6:03 pm-5:24 pm
1 stop23h 21m
$434
Showing 1-10 of 38 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 June.
| 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 $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 June 18, 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 55% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Chicago to Valparaiso, Florida?
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.
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 June 18, 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.
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
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 June 18, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 18, 2026.
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Other flights to Valparaiso
Explore flights to Valparaiso departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 18, 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 June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$344 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$234 | Average$413 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$463 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$295 | Average$421 | FlexibilityNo cancel fee | On-time71% |