Cheap Flights from Chicago to Valparaiso
Cheap Flights from Chicago to Valparaiso
Looking for cheap flights from Chicago to Valparaiso? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Valparaiso vary by season, cabin, and date, but available award flights can start around 7,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Valparaiso for specific travel dates.
2026-11-07
ORD - VPS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-08
ORD - VPS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-09
ORD - VPS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
ORD - VPS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-11
ORD - VPS
Economy | Non stop | 6 left
From 7,500 Pts + $25.6
2026-11-13
ORD - VPS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to Valparaiso flight facts
Distance
792 mi
1,275 km in a straight line
Estimated flight time
about 2h
In the air, for the straight-line distance
Time difference
Same time zone
Valparaiso is in the same time zone as Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Valparaiso
VPS · Destin-Ft Walton Beach
Nearby airport alternatives
Flights Chicago - Pensacola · Pensacola is 39 mi from Valparaiso
Flights Chicago - Panama City · Panama City is 44 mi from Valparaiso
Flights Milwaukee - Valparaiso · Milwaukee is 73 mi from Chicago
Flights South Bend - Valparaiso · South Bend is 86 mi from Chicago
Flights Peoria - Valparaiso · Peoria is 123 mi from Chicago
Flights Chicago - Tallahassee · Tallahassee is 130 mi from Valparaiso
Premium cabin flights from Chicago to Valparaiso
Premium cabin
2026-11-14
ORD - VPS
First | Non stop | 2 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-16
ORD - VPS
First | Non stop | 6 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-17
ORD - VPS
First | Non stop | 3 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-18
ORD - VPS
First | 1 Stop | 6 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-06
ORD - VPS
First | 1 Stop | 3 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-12
ORD - VPS
First | 1 Stop | 1 left
From 35,000 Pts + $25.6
Selected hotels for your next stay
No hotels available at the moment. Check back soon!
Frequently Asked Questions
The cheapest route from Chicago to Valparaiso depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Valparaiso.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Valparaiso.
Chicago and Valparaiso are about 792 miles (1,275 km) apart in a straight line.
Flying the 792-mile straight-line distance takes about 2h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Valparaiso is in the same time zone as Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Valparaiso: Destin-Ft Walton Beach (VPS).
Travelers searching this route also look at other popular routes into Valparaiso, plus the return trip when we track it. Fares and award space change daily.
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points travel planning experience. Yeah!
