$71+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — CHI
May 31 — Jun 71
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Valparaiso to Chicago
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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 May 1, 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 May 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 8/282:10 pm
VPS
- MDW
Nonstop2h 15m
Allegiant Air
Mon 9/76:29 pm
MDW
- VPS
Nonstop2h 11m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/156:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 4/29![Allegiant Air logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/221:19 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$132
This Cheapflightsfares deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Allegiant Air
Deal found 4/29![Allegiant Air logo]()
$146
This Cheapflightsfares deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Thu 5/77:08 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 4/27![Allegiant Air logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:23 pm
VPS
- MDW
2 stops38h 46m
Multiple Airlines
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 5/35:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:40 pm
VPS
- MDW
2 stops27h 22m
Multiple Airlines
Mon 6/19:30 pm
MDW
- VPS
Nonstop2h 07m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/227:40 pm
VPS
- MDW
2 stops26h 22m
Multiple Airlines
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Multiple Airlines
Sat 5/3011:59 am
MDW
- VPS
2 stops34h 20m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:23 pm
VPS
- MDW
2 stops38h 46m
Multiple Airlines
Mon 6/299:23 pm
MDW
- VPS
Nonstop2h 13m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
VPS
- ORD
2 stops13h 26m
Multiple Airlines
Wed 6/39:37 pm
ORD
- VPS
1 stop19h 47m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$319
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 May 1, 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 May 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:14 pm
VPS
- MDW
Nonstop2h 21m
Multiple Airlines
Sun 8/168:20 pm
MDW
- VPS
2 stops23h 57m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:00 pm
VPS
- MDW
1 stop8h 20m
Southwest
Wed 6/34:50 pm
MDW
- VPS
1 stop4h 10m
Southwest
Deal found 4/27![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:45 pm
VPS
- ORD
1 stop5h 47m
Delta
Tue 7/71:44 pm
ORD
- VPS
1 stop4h 58m
Delta
Deal found 4/28![Delta logo]()
$375
This American Airlines deal was found by Cheapflights users on 5/1. 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 7/111:16 am
VPS
- ORD
Nonstop2h 41m
American Airlines
Thu 7/98:29 am
ORD
- VPS
Nonstop2h 32m
American Airlines
Deal found 5/1![American Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
VPS
- MDW
1 stop4h 09m
Delta
Tue 7/75:10 pm
MDW
- VPS
1 stop6h 19m
Delta
Deal found 4/28![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:35 am
VPS
- MDW
2 stops10h 05m
Southwest
Wed 7/811:25 am
MDW
- VPS
2 stops9h 55m
Southwest
Deal found 4/27![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:19 am
VPS
- MDW
1 stop6h 21m
Delta
Wed 7/86:00 am
MDW
- VPS
1 stop4h 29m
Delta
Deal found 4/27![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 4/30. 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 6/17:20 am
VPS
- ORD
1 stop5h 30m
Southwest
Tue 6/22:40 pm
ORD
- VPS
1 stop6h 20m
Southwest
Deal found 4/30![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:00 am
VPS
- MDW
1 stop4h 09m
Delta
Tue 7/712:41 pm
MDW
- VPS
1 stop6h 01m
Delta
Deal found 4/28![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 4/30. 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 6/16:15 pm
VPS
- MDW
1 stop5h 15m
Southwest
Tue 6/24:50 pm
MDW
- VPS
1 stop4h 10m
Southwest
Deal found 4/30![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:20 am
VPS
- ORD
1 stop5h 30m
Southwest
Mon 6/12:40 pm
ORD
- VPS
1 stop6h 25m
Southwest
Deal found 4/28![Southwest logo]()
$389
This Delta deal was found by Cheapflights users on 4/30. 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 8/511:10 am
VPS
- ORD
1 stop7h 35m
Delta
Sun 8/95:15 am
ORD
- VPS
1 stop5h 10m
Delta
Deal found 4/30![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 4/30. 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 7/16:00 am
VPS
- MDW
1 stop4h 09m
Delta
Thu 7/911:05 am
MDW
- VPS
1 stop5h 16m
Delta
Deal found 4/30![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 5/1. 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 5/286:15 pm
VPS
- MDW
1 stop5h 15m
Southwest
Thu 6/41:00 pm
MDW
- VPS
2 stops8h 05m
Southwest
Deal found 5/1![Southwest logo]()
$395
This Delta deal was found by Cheapflights users on 4/30. 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 8/56:00 am
VPS
- MDW
1 stop4h 03m
Delta
Sun 8/96:05 am
MDW
- VPS
1 stop6h 24m
Delta
Deal found 4/30![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 5/1. 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 7/16:00 am
VPS
- ORD
1 stop6h 36m
Delta
Thu 7/98:03 am
ORD
- VPS
1 stop4h 26m
Delta
Deal found 5/1![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:17 pm
VPS
- ORD
1 stop5h 18m
Delta
Mon 6/86:30 am
ORD
- VPS
1 stop6h 40m
Delta
Deal found 4/28![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:00 am
VPS
- ORD
1 stop4h 13m
Delta
Mon 6/296:30 am
ORD
- VPS
1 stop6h 40m
Delta
Deal found 4/29![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:45 pm
VPS
- ORD
1 stop4h 08m
Delta
Tue 5/199:49 am
ORD
- VPS
1 stop6h 51m
Delta
Deal found 4/26![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:30 am
VPS
- ORD
1 stop5h 31m
Delta
Mon 5/187:07 am
ORD
- VPS
1 stop5h 20m
Delta
Deal found 4/26![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
VPS
- ORD
1 stop4h 16m
Delta
Wed 5/207:07 am
ORD
- VPS
1 stop6h 53m
Delta
Deal found 4/26![Delta logo]()
$432
Last-minute flights from Valparaiso to ChicagoDiscover last-minute flight deals from Valparaiso to Chicago. Data last updated May 1, 2026 and is based on user searches.
Discover last-minute flight deals from Valparaiso to Chicago. Data last updated May 1, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Thu 5/77:08 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 4/27![Allegiant Air logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:05 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Sun 5/35:47 pm
MDW
- VPS
Nonstop2h 09m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$206
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/221:19 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/227:40 pm
VPS
- MDW
2 stops26h 22m
Multiple Airlines
Mon 5/259:30 pm
MDW
- VPS
Nonstop2h 07m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:17 pm
VPS
- ORD
1 stop7h 09m
Delta
Tue 6/29:49 am
ORD
- VPS
1 stop4h 11m
Delta
Deal found 4/28![Delta logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:40 pm
VPS
- MDW
2 stops27h 22m
Multiple Airlines
Mon 6/19:30 pm
MDW
- VPS
Nonstop2h 07m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:20 am
VPS
- ORD
Nonstop2h 43m
American Airlines
Mon 6/14:45 pm
ORD
- VPS
1 stop5h 08m
American Airlines
Deal found 4/28![American Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Multiple Airlines
Sat 5/3011:59 am
MDW
- VPS
2 stops34h 20m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Multiple Airlines
Wed 6/312:04 pm
MDW
- VPS
3 stops35h 11m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
VPS
- ORD
2 stops13h 26m
Multiple Airlines
Wed 6/39:37 pm
ORD
- VPS
1 stop19h 47m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:13 am
VPS
- ORD
1 stop5h 05m
American Airlines
Sat 5/308:15 am
ORD
- VPS
Nonstop2h 35m
American Airlines
Deal found 4/28![American Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:55 pm
VPS
- ORD
1 stop6h 58m
Delta
Wed 6/38:10 am
ORD
- VPS
1 stop5h 50m
Delta
Deal found 4/27![Delta logo]()
$375
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 May 1, 2026.
Search for one-way flight options from Valparaiso to Chicago. Find affordable one-way fares based on user searches. Data last updated May 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/296:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$71
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 6/226:12 pm
VPS
- MDW
Nonstop2h 21m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$88
This Trip.com deal was found by Cheapflights users on 4/30. 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 5/74:01 pm
VPS
- MDW
Nonstop2h 17m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/143:12 pm
VPS
- MDW
1 stop28h 18m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 4/27![Allegiant Air logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:24 pm
VPS
- ORD
2 stops34h 00m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:23 pm
VPS
- ORD
2 stops23h 30m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/308:24 pm
VPS
- ORD
2 stops35h 31m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:40 am
VPS
- ORD
2 stops22h 44m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/256:21 pm
VPS
- MDW
Nonstop2h 19m
Allegiant Air
Deal found 4/30![Allegiant Air logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 7/231:04 pm
VPS
- ORD
1 stop7h 48m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/17:51 pm
VPS
- ORD
2 stops23h 38m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$153
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 May 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $118 (Cheapflightsfares) |
One-way from | $71 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $103 |
Good round-trip deal | $108 or less |
Good one-way deal | $246 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 May 1, 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
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 8/14
6:14 pm-8:35 pm
Nonstop2h 21m
Chicago Midway
Sun 8/16
8:20 pm-8:17 pm
2 stops23h 57m
$323
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 5/29
2:00 pm-10:20 pm
1 stop8h 20m
Chicago Midway
Wed 6/3
4:50 pm-9:00 pm
1 stop4h 10m
$374
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Fri 7/3
2:45 pm-8:32 pm
1 stop5h 47m
Chicago O'Hare Intl
Tue 7/7
1:44 pm-6:42 pm
1 stop4h 58m
$375
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Wed 7/1
6:00 am-10:09 am
1 stop4h 09m
Chicago Midway
Tue 7/7
5:10 pm-11:29 pm
1 stop6h 19m
$375
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 7/4
9:19 am-3:40 pm
1 stop6h 21m
Chicago Midway
Wed 7/8
6:00 am-10:29 am
1 stop4h 29m
$375
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 7/3
6:00 am-10:09 am
1 stop4h 09m
Chicago Midway
Tue 7/7
12:41 pm-6:42 pm
1 stop6h 01m
$375
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 7/4
10:35 am-8:40 pm
2 stops10h 05m
Chicago Midway
Wed 7/8
11:25 am-9:20 pm
2 stops9h 55m
$386
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Mon 6/1
7:20 am-12:50 pm
1 stop5h 30m
Chicago O'Hare Intl
Tue 6/2
2:40 pm-9:00 pm
1 stop6h 20m
$388
ValparaisoChicago
VPS - MDW
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 6/1
6:15 pm-11:30 pm
1 stop5h 15m
Chicago Midway
Tue 6/2
4:50 pm-9:00 pm
1 stop4h 10m
$388
ValparaisoChicago
VPS - ORD
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 5/28
7:20 am-12:50 pm
1 stop5h 30m
Chicago O'Hare Intl
Mon 6/1
2:40 pm-9:05 pm
1 stop6h 25m
$389
Showing 1-10 of 41 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 May.
| 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, May is the cheapest month in which you can book a flight from Valparaiso, Florida to Chicago (average of $48). Flying from Valparaiso, Florida to Chicago in December is currently the most expensive (average of $376). 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 May 1, 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.
Weekly flight availability from Valparaiso, Florida to Chicago
Explore weekly flight availability from Valparaiso to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 1, 2026.
The most flights from VPS to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Valparaiso, Florida to Chicago?
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 May 1, 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.
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 1, 2026.
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Valparaiso and Chicago flights
Browse other Valparaiso and Chicago flight options. Last updated on May 1, 2026.
Other flights from Valparaiso
Browse through other flights departing from Valparaiso. Flights are based on user searches made on Cheapflights and were last updated on May 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 May 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$188 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$157 | Average$384 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$400 | FlexibilityNo cancel fee | On-time63% |