Cheap Flights from Chicago to Guadalajara
Looking for cheap flights from Chicago to Guadalajara? 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 Guadalajara vary by season and date, but economy flights can start around 11,000–22,800 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 Guadalajara for specific travel dates.
2026-06-08
ORD - GDL
Economy | Non stop | 9+ left
From 20,000 Pts + $61.3
2026-06-08
ORD - GDL
Economy | 2 Stops
From 11,000 Pts + $66.7
2026-06-08
ORD - GDL
Economy | Non stop
From 22,800 Pts + $107.1
2026-06-09
ORD - GDL
Economy | 2 Stops | 8 left
From 18,150 Pts + $83
2026-06-09
ORD - GDL
Economy | 1 Stop
From 11,000 Pts + $61.1
2026-06-09
ORD - GDL
Economy | 1 Stop | 9+ left
From 22,100 Pts + $61.3
Premium cabin flights from Chicago to Guadalajara
Premium cabin
2026-06-08
ORD - GDL
Business | 2 Stops | 7 left
From 47,300 Pts + $130.7
Premium cabin
2026-06-08
ORD - GDL
Business | Non stop | 9+ left
From 35,000 Pts + $61.3
Premium cabin
2026-06-08
ORD - GDL
Business | Non stop
From 46,300 Pts + $107.1
Premium cabin
2026-06-09
ORD - GDL
Business | Non stop | 9+ left
From 35,700 Pts + $61.3
Premium cabin
2026-06-09
ORD - GDL
First | 1 Stop | 9+ left
From 49,700 Pts + $61.3
Premium cabin
2026-06-09
ORD - GDL
Business | Non stop
From 46,300 Pts + $107.1
Selected hotels for your next stay
Guadalajara (Mexico)
Hotel Indigo Guadalajara Expo
From 18,000 Pts or $133
GUADALAJARA (Mexico)
InterContinental Hotels Presidente Guadalajara
From 18,000 Pts or $138
Guadalajara (Mexico)
JW Marriott Hotel Guadalajara
From Pts or $283
Frequently Asked Questions
The cheapest route from Chicago to Guadalajara 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 Guadalajara.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Guadalajara.
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