$88+ 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 9 — Apr 161
Round-trip
1 adult, Economy
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Find cheap flights from Valparaiso to Chicago with Cheapflights
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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 10, 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 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/126:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/159:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 3/6![Allegiant Air logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/9![Allegiant Air logo]()
$111
This Booking.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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.
Thu 4/92:40 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/125:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/7![Allegiant Air logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/137:16 pm
VPS
- MDW
1 stop18h 40m
Allegiant Air
Mon 6/159:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 3/6![Allegiant Air logo]()
$195
This Cheapflightsfares deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/125:37 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Sun 3/158:43 pm
MDW
- VPS
Nonstop2h 08m
Allegiant Air
Deal found 3/6![Allegiant Air logo]()
$249
This Gotogate deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:07 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Sun 3/229:13 pm
MDW
- VPS
Nonstop2h 08m
Allegiant Air
Deal found 3/9![Allegiant Air logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/98:16 am
VPS
- MDW
3 stops14h 05m
Multiple Airlines
Sun 4/125:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/134:50 pm
VPS
- MDW
2 stops25h 46m
Multiple Airlines
Mon 6/159:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/2711:20 am
VPS
- ORD
Nonstop2h 43m
American Airlines
Wed 6/38:15 am
ORD
- VPS
Nonstop2h 35m
American Airlines
Deal found 3/9![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/2711:20 am
VPS
- ORD
Nonstop2h 43m
American Airlines
Tue 6/25:00 am
ORD
- VPS
1 stop6h 30m
American Airlines
Deal found 3/9![American Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/129:03 pm
VPS
- MDW
2 stops23h 03m
Multiple Airlines
Mon 6/159:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Wed 6/32:40 pm
ORD
- VPS
1 stop6h 20m
Southwest
Deal found 3/9![Southwest logo]()
$355
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 10, 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 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 3/5![Allegiant Air logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/134:50 pm
VPS
- MDW
2 stops25h 46m
Multiple Airlines
Mon 6/159:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Wed 6/311:55 am
ORD
- VPS
2 stops9h 05m
Southwest
Deal found 3/9![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 7/11:10 pm
VPS
- ORD
1 stop7h 08m
Delta
Thu 7/96:00 am
ORD
- VPS
1 stop4h 11m
Delta
Deal found 3/6![Delta logo]()
$374
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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.
Thu 4/2312:05 pm
VPS
- ORD
Nonstop2h 48m
American Airlines
Mon 4/275:20 pm
ORD
- VPS
1 stop6h 30m
American Airlines
Deal found 3/8![American Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 3/8![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 7/12:40 pm
VPS
- MDW
1 stop7h 05m
Delta
Thu 7/96:00 am
MDW
- VPS
1 stop4h 11m
Delta
Deal found 3/9![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
Sun 5/244:00 pm
VPS
- MDW
1 stop5h 25m
Southwest
Tue 5/267:00 am
MDW
- VPS
1 stop6h 10m
Southwest
Deal found 3/9![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/122:25 pm
VPS
- ORD
1 stop7h 09m
Delta
Mon 6/156:00 am
ORD
- VPS
1 stop6h 26m
Delta
Deal found 3/6![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/236:00 am
VPS
- MDW
1 stop3h 56m
Delta
Mon 4/276:00 am
MDW
- VPS
1 stop4h 59m
Delta
Deal found 3/5![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:15 am
VPS
- ORD
2 stops11h 10m
Southwest
Tue 6/211:55 am
ORD
- VPS
2 stops9h 05m
Southwest
Deal found 3/9![Southwest logo]()
$399
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/6![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/1512:35 pm
VPS
- ORD
2 stops9h 20m
Southwest
Sun 5/177:35 pm
ORD
- VPS
2 stops17h 45m
Southwest
Deal found 3/9![Southwest logo]()
$410
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/27:20 am
VPS
- ORD
2 stops11h 15m
Southwest
Thu 4/92:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Deal found 3/5![Southwest logo]()
$432
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 6/55:45 pm
VPS
- ORD
1 stop4h 08m
Delta
Sat 6/136:00 am
ORD
- VPS
1 stop4h 12m
Delta
Deal found 3/5![Delta logo]()
$475
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/137:00 am
VPS
- ORD
1 stop5h 50m
Southwest
Mon 6/157:20 pm
ORD
- VPS
2 stops14h 20m
Southwest
Deal found 3/6![Southwest logo]()
$433
Last-minute flights from Valparaiso to ChicagoDiscover last-minute flight deals from Valparaiso to Chicago. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Valparaiso to Chicago. Data last updated March 10, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/125:37 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Sun 3/158:43 pm
MDW
- VPS
Nonstop2h 08m
Allegiant Air
Deal found 3/6![Allegiant Air logo]()
$249
This American Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/171:00 pm
VPS
- ORD
Nonstop2h 44m
American Airlines
Tue 3/243:16 pm
ORD
- VPS
1 stop6h 59m
American Airlines
Deal found 3/9![American Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/173:00 pm
VPS
- ORD
1 stop6h 10m
Delta
Tue 3/247:10 am
ORD
- VPS
1 stop4h 49m
Delta
Deal found 3/9![Delta logo]()
$421
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 3/177:15 am
VPS
- ORD
1 stop5h 35m
Southwest
Sun 3/222:40 pm
ORD
- VPS
1 stop6h 35m
Southwest
Deal found 3/7![Southwest logo]()
$436
This Gotogate deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:07 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Sun 3/229:13 pm
MDW
- VPS
Nonstop2h 08m
Allegiant Air
Deal found 3/9![Allegiant Air logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/196:35 am
VPS
- MDW
1 stop6h 27m
Multiple Airlines
Sun 3/229:13 pm
MDW
- VPS
Nonstop2h 08m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$412
This Booking.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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.
Thu 4/92:40 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 4/125:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 3/7![Allegiant Air logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/98:16 am
VPS
- MDW
3 stops14h 05m
Multiple Airlines
Sun 4/125:47 pm
MDW
- VPS
Nonstop2h 09m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$304
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/97:20 am
VPS
- MDW
2 stops7h 45m
Southwest
Sun 4/129:45 pm
MDW
- VPS
2 stops14h 05m
Southwest
Deal found 3/7![Southwest logo]()
$405
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 3/10![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/236:00 am
VPS
- MDW
1 stop3h 56m
Delta
Mon 4/276:00 am
MDW
- VPS
1 stop4h 59m
Delta
Deal found 3/9![Delta logo]()
$393
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/9![Allegiant Air logo]()
$111
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 10, 2026.
Search for one-way flight options from Valparaiso to Chicago. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/265:37 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Deal found 3/6![Allegiant Air logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/196:07 pm
VPS
- MDW
Nonstop2h 16m
Allegiant Air
Deal found 3/9![Allegiant Air logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/77:30 am
VPS
- ORD
1 stop28h 12m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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
Deal found 3/5![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:45 am
VPS
- ORD
2 stops29h 29m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:00 am
VPS
- ORD
2 stops37h 17m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:00 am
VPS
- ORD
2 stops37h 17m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/68:00 am
VPS
- ORD
2 stops49h 50m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$162
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 3/3112:35 pm
VPS
- MDW
2 stops7h 20m
Southwest
Deal found 3/5![Southwest logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:00 am
VPS
- MDW
2 stops35h 31m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/810:25 am
VPS
- MDW
1 stop5h 00m
Southwest
Deal found 3/7![Southwest logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/22:40 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 3/5![Allegiant Air logo]()
$181
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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $101 (Cheapflightsfares) |
One-way from | $88 (Cheapflightsfares) |
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 10, 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
$118
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 6/13
4:50 pm-6:36 pm
2 stops25h 46m
Chicago Midway
Mon 6/15
9:23 pm-11:36 pm
Nonstop2h 13m
$317
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 5/27
7:15 am-12:50 pm
1 stop5h 35m
Chicago O'Hare Intl
Wed 6/3
11:55 am-9:00 pm
2 stops9h 05m
$361
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 4/22
7:15 am-12:50 pm
1 stop5h 35m
Chicago O'Hare Intl
Mon 4/27
2:40 pm-9:05 pm
1 stop6h 25m
$369
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Wed 7/1
1:10 pm-8:18 pm
1 stop7h 08m
Chicago O'Hare Intl
Thu 7/9
6:00 am-10:11 am
1 stop4h 11m
$374
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Wed 7/1
2:40 pm-9:45 pm
1 stop7h 05m
Chicago Midway
Thu 7/9
6:00 am-10:11 am
1 stop4h 11m
$374
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sun 5/24
4:00 pm-9:25 pm
1 stop5h 25m
Chicago Midway
Tue 5/26
7:00 am-1:10 pm
1 stop6h 10m
$374
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 4/23
12:05 pm-2:53 pm
Nonstop2h 48m
Chicago O'Hare Intl
Mon 4/27
5:20 pm-11:50 pm
1 stop6h 30m
$384
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Fri 6/12
2:25 pm-9:34 pm
1 stop7h 09m
Chicago O'Hare Intl
Mon 6/15
6:00 am-12:26 pm
1 stop6h 26m
$393
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 4/23
6:00 am-9:56 am
1 stop3h 56m
Chicago Midway
Mon 4/27
6:00 am-10:59 am
1 stop4h 59m
$393
Showing 1-10 of 35 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 10, 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 10, 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
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
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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 10, 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% |