Find Cheap Point Flights to Chicago
Looking for cheap point flights to Chicago? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can quickly compare options and spot the lowest mileage routes. 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 to Chicago vary by season, cabin, and departure city, but available award flights can start around 3,600–4,500 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 to Chicago for specific travel dates.
2026-10-20
MSP - ORD
Economy | Non stop | 9+ left
From 3,600 Pts + $5.6
2026-10-21
MSP - ORD
Economy | Non stop | 2 left
From 3,600 Pts + $5.6
2026-08-26
DCA - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-08-26
EWR - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-08-26
AVP - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-08-27
PHL - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
Premium cabin flights from New York
Premium cabin
2026-08-26
JFK - ORD
First | 1 Stop | 2 left
From 15,000 Pts + $25.6
Premium cabin
2026-08-26
PIT - ORD
First | Non stop
From 17,500 Pts + $5.6
Premium cabin
2026-08-26
MSP - ORD
First | Non stop
From 17,500 Pts + $5.6
Premium cabin
2026-08-26
SCE - ORD
First | 1 Stop
From 21,000 Pts + $5.6
Premium cabin
2026-08-26
JFK - ORD
First | Non stop
From 21,500 Pts + $5.6
Premium cabin
2026-08-26
JFK - ORD
First | Non stop | 3 left
From 26,300 Pts + $5.6
Flights departing from all over the world
Minneapolis, MN - Chicago
From 3,600 Pts + $5.6
New York, NY - Chicago
From 4,500 Pts + $25.6
Baltimore, MD - Chicago
From 4,500 Pts + $25.6
Columbia, MO - Chicago
From 4,500 Pts + $25.6
Cincinnati, OH - Chicago
From 4,500 Pts + $25.6
Traverse City, MI - Chicago
From 4,500 Pts + $25.6
Philadelphia, PA - Chicago
From 4,500 Pts + $25.6
Birmingham, AL - Chicago
From 4,500 Pts + $25.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $445
Chicago (United States)
Thompson Chicago
From 15,000 Pts or $275
Vernon Hills (United States)
Hotel Indigo Chicago-Vernon Hills
From 18,000 Pts or $137
Frequently Asked Questions
The cheapest way to fly to Chicago depends on award space, travel dates, and transfer partner pricing. PointsYeah helps compare bank and airline programs side by side so you can see the best points and cash options in one place.
Search the metro or city code for Chicago when available to compare all nearby airport options in one route summary. That makes it easier to see award availability without checking each airport separately.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights to Chicago.
Our mission is to provide
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Our mission is to provide the simplest and best
points travel planning experience. Yeah!
