$69+ Cheap flights from Valparaiso, FL (VPS) to Chicago (CHI)
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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
Apr 17 — Apr 241
Round-trip
1 adult, Economy
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Find cheap flights from Valparaiso to Chicago 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
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Cheapest flights from Valparaiso to ChicagoExplore the most affordable flight options available from Valparaiso to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 18, 2026.
Explore the most affordable flight options available from Valparaiso to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/18![Allegiant Air logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Thu 5/75:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/13![Allegiant Air logo]()
$111
This Booking.com deal was found by Cheapflights users on 3/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/295:37 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Thu 4/25:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/14![Allegiant Air logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:47 am
VPS
- MDW
2 stops14h 32m
Multiple Airlines
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:00 am
VPS
- MDW
3 stops35h 31m
Multiple Airlines
Thu 4/167:12 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Fri 7/246:05 pm
VPS
- MDW
Nonstop2h 20m
Multiple Airlines
Tue 8/49:11 pm
MDW
- VPS
3 stops46h 37m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Sun 3/298:19 pm
VPS
- MDW
2 stops23h 28m
Multiple Airlines
Thu 4/25:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2611:17 am
VPS
- ORD
Nonstop2h 43m
American Airlines
Tue 6/28:12 am
ORD
- VPS
Nonstop2h 35m
American Airlines
Deal found 3/17![American Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:08 am
VPS
- ORD
2 stops24h 15m
Multiple Airlines
Sat 5/912:53 pm
ORD
- VPS
1 stop24h 57m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 3/17. 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.
Tue 5/267:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Tue 6/22:40 pm
ORD
- VPS
1 stop6h 20m
Southwest
Deal found 3/17![Southwest logo]()
$373
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/13:53 pm
VPS
- ORD
1 stop8h 49m
American Airlines
Thu 7/98:26 am
ORD
- VPS
Nonstop2h 36m
American Airlines
Deal found 3/17![American Airlines logo]()
$385
This Sun Country Air deal was found by Cheapflights users on 3/17. 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.
Fri 5/112:16 pm
VPS
- ORD
1 stop6h 50m
Sun Country Air
Fri 5/88:06 pm
ORD
- VPS
1 stop21h 01m
Sun Country Air
Deal found 3/17![Sun Country Air logo]()
$386
Best flights from Valparaiso to ChicagoDiscover carefully curated flight deals from Valparaiso to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 18, 2026.
Discover carefully curated flight deals from Valparaiso to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 18, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Thu 5/75:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/13![Allegiant Air logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Sun 3/298:19 pm
VPS
- MDW
2 stops23h 28m
Multiple Airlines
Thu 4/25:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 3/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Tue 6/22:40 pm
ORD
- VPS
1 stop6h 20m
Southwest
Deal found 3/14![Southwest logo]()
$375
This Sun Country Air deal was found by Cheapflights users on 3/17. 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.
Fri 5/112:16 pm
VPS
- ORD
1 stop6h 50m
Sun Country Air
Fri 5/88:06 pm
ORD
- VPS
1 stop21h 01m
Sun Country Air
Deal found 3/17![Sun Country Air logo]()
$386
This Delta deal was found by Cheapflights users on 3/18. 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.
Fri 4/175:05 pm
VPS
- MDW
1 stop5h 23m
Delta
Sun 4/196:00 am
MDW
- VPS
1 stop4h 59m
Delta
Deal found 3/18![Delta logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Mon 3/308:42 pm
VPS
- MDW
3 stops24h 12m
Multiple Airlines
Thu 4/25:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$359
This Sun Country Air deal was found by Cheapflights users on 3/13. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:07 pm
VPS
- ORD
1 stop24h 59m
Sun Country Air
Thu 5/78:06 pm
ORD
- VPS
1 stop15h 00m
Sun Country Air
Deal found 3/13![Sun Country Air logo]()
$396
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 7/292:30 pm
VPS
- MDW
1 stop5h 05m
Southwest
Mon 8/31:00 pm
MDW
- VPS
2 stops8h 05m
Southwest
Deal found 3/17![Southwest logo]()
$400
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:05 pm
VPS
- MDW
1 stop5h 23m
Delta
Mon 4/275:21 pm
MDW
- VPS
1 stop5h 58m
Delta
Deal found 3/13![Delta logo]()
$433
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:20 am
VPS
- ORD
1 stop5h 30m
Southwest
Sun 4/262:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Deal found 3/18![Southwest logo]()
$408
This Delta deal was found by Cheapflights users on 3/16. 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.
Fri 4/245:05 pm
VPS
- MDW
1 stop5h 23m
Delta
Mon 4/276:00 am
MDW
- VPS
1 stop4h 59m
Delta
Deal found 3/16![Delta logo]()
$433
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2312:35 pm
VPS
- MDW
2 stops8h 40m
Southwest
Sun 4/266:55 am
MDW
- VPS
2 stops8h 20m
Southwest
Deal found 3/18![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 3/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Sat 4/42:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Deal found 3/15![Southwest logo]()
$441
This Southwest deal was found by Cheapflights users on 3/17. 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.
Wed 4/17:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Sun 4/52:40 pm
ORD
- VPS
1 stop6h 35m
Southwest
Deal found 3/17![Southwest logo]()
$456
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/212:35 pm
VPS
- ORD
2 stops9h 20m
Southwest
Mon 4/62:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Deal found 3/18![Southwest logo]()
$477
Last-minute flights from Valparaiso to ChicagoDiscover last-minute flight deals from Valparaiso to Chicago. Data last updated March 18, 2026 and is based on user searches.
Discover last-minute flight deals from Valparaiso to Chicago. Data last updated March 18, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 3/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/295:37 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Thu 4/25:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/14![Allegiant Air logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Sun 3/298:19 pm
VPS
- MDW
2 stops23h 28m
Multiple Airlines
Thu 4/25:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Mon 3/308:42 pm
VPS
- MDW
2 stops18h 51m
Multiple Airlines
Thu 4/25:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:00 am
VPS
- MDW
3 stops35h 31m
Multiple Airlines
Thu 4/167:12 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Mon 4/138:00 am
VPS
- ORD
2 stops33h 00m
Multiple Airlines
Mon 4/207:05 pm
ORD
- VPS
1 stop18h 01m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 3/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:05 pm
VPS
- ORD
Nonstop2h 48m
American Airlines
Mon 4/279:41 am
ORD
- VPS
Nonstop2h 34m
American Airlines
Deal found 3/18![American Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 3/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:05 pm
VPS
- ORD
Nonstop2h 48m
American Airlines
Sun 4/266:57 am
ORD
- VPS
1 stop7h 34m
American Airlines
Deal found 3/18![American Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Mon 4/272:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Deal found 3/18![Southwest logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/18![Allegiant Air logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:47 am
VPS
- MDW
2 stops14h 32m
Multiple Airlines
Sun 4/265:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$225
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Thu 5/75:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/13![Allegiant Air logo]()
$111
This Sun Country Air deal was found by Cheapflights users on 3/17. 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 4/306:07 pm
VPS
- ORD
1 stop24h 59m
Sun Country Air
Thu 5/78:06 pm
ORD
- VPS
1 stop15h 00m
Sun Country Air
Deal found 3/17![Sun Country Air logo]()
$366
One-way flights from Valparaiso to ChicagoSearch for one-way flight options from Valparaiso to Chicago. Find affordable one-way fares based on user searches. Data last updated March 18, 2026.
Search for one-way flight options from Valparaiso to Chicago. Find affordable one-way fares based on user searches. Data last updated March 18, 2026.
This Trip.com deal was found by Cheapflights users on 3/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/265:37 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Deal found 3/14![Allegiant Air logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:58 pm
VPS
- ORD
2 stops38h 25m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:40 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 3/16![Allegiant Air logo]()
$148
This Trip.com deal was found by Cheapflights users on 3/15. 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.
Sun 3/295:37 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Deal found 3/15![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:16 am
VPS
- ORD
2 stops38h 38m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Sun 8/23:08 pm
VPS
- MDW
1 stop23h 30m
Allegiant Air
Deal found 3/14![Allegiant Air logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Mon 4/138:00 am
VPS
- ORD
3 stops57h 00m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:16 am
VPS
- ORD
2 stops39h 43m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$169
This Sun Country Air deal was found by Cheapflights users on 3/13. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:06 pm
VPS
- ORD
1 stop7h 00m
Sun Country Air
Deal found 3/13![Sun Country Air logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:30 am
VPS
- ORD
2 stops15h 57m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 3/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 pm
VPS
- MDW
1 stop4h 35m
Southwest
Deal found 3/15![Southwest logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Fri 4/177:36 pm
VPS
- MDW
3 stops26h 38m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$205
Find flight deals from Valparaiso to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $97 (Kiwi.com) |
One-way from | $69 (Trip.com) |
Popular in | December |
Cheapest in | May |
Average price | $345 |
Good round-trip deal | $232 or less |
Good one-way deal | $287 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Valparaiso to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 18, 2026.
Use the filters below to find and compare flights from Valparaiso to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 4/30
4:05 pm-6:22 pm
Nonstop2h 17m
Chicago Midway
Thu 5/7
5:47 pm-7:56 pm
Nonstop2h 09m
$111
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sun 3/29
8:19 pm-7:47 pm
2 stops23h 28m
Chicago Midway
Thu 4/2
5:47 pm-7:56 pm
Nonstop2h 09m
$354
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 3/30
8:42 pm-8:54 pm
3 stops24h 12m
Chicago Midway
Thu 4/2
5:47 pm-7:56 pm
Nonstop2h 09m
$359
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Tue 5/26
7:15 am-12:50 pm
1 stop5h 35m
Chicago O'Hare Intl
Tue 6/2
2:40 pm-9:00 pm
1 stop6h 20m
$375
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Fri 5/1
12:16 pm-7:06 pm
1 stop6h 50m
Chicago O'Hare Intl
Fri 5/8
8:06 pm-5:07 pm
1 stop21h 01m
$386
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 4/30
6:07 pm-7:06 pm
1 stop24h 59m
Chicago O'Hare Intl
Thu 5/7
8:06 pm-11:06 am
1 stop15h 00m
$396
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Wed 7/29
2:30 pm-7:35 pm
1 stop5h 05m
Chicago Midway
Mon 8/3
1:00 pm-9:05 pm
2 stops8h 05m
$400
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 4/23
7:20 am-12:50 pm
1 stop5h 30m
Chicago O'Hare Intl
Sun 4/26
2:40 pm-9:05 pm
1 stop6h 25m
$408
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 4/17
5:05 pm-10:28 pm
1 stop5h 23m
Chicago Midway
Sun 4/19
6:00 am-10:59 am
1 stop4h 59m
$413
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 4/23
12:35 pm-9:15 pm
2 stops8h 40m
Chicago Midway
Sun 4/26
6:55 am-3:15 pm
2 stops8h 20m
$419
Showing 1-10 of 31 resultsSorted by cheapest first
Compare providers for flights from Valparaiso to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Valparaiso to Chicago in March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Valparaiso, Florida-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Valparaiso, Florida-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Valparaiso, Florida-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Valparaiso, Florida-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Valparaiso, Florida-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Valparaiso to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Valparaiso with our price prediction graph.
VPS-CHI
VPS-MDW
VPS-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Valparaiso to Chicago
VPS-CHI
VPS-MDW
VPS-ORD
What is the cheapest month to book a flight from Valparaiso, Florida to Chicago?
Currently, June is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $112). Flying from Valparaiso, Florida to Chicago in December is currently the most expensive (average of $228). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from VPS to CHI?
Find hourly flight availability from Valparaiso to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 18, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Valparaiso, Florida to Chicago as you normally would.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated March 18, 2026.
Get a feel of what it's like to fly with Southwest,Allegiant Air, andAmerican Airlines from Valparaiso to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Related info for your journey
Find useful and relevant information for your journey from Valparaiso to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Valparaiso and Chicago flights
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Top 3 airlines flying from Valparaiso to Chicago
Discover the top 3 airlines that operate flights from Valparaiso to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$188 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$157 | Average$380 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$400 | FlexibilityNo cancel fee | On-time63% |