Cheapest Flights to Chicago
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 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.
2026-11-05
BHM - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-05
COU - ORD
Economy | Non stop | 7 left
From 4,500 Pts + $25.6
2026-11-05
AZO - ORD
Economy | Non stop | 8 left
From 4,500 Pts + $25.6
2026-11-05
AVL - ORD
Economy | Non stop | 3 left
From 4,500 Pts + $25.6
2026-11-05
CID - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-05
YTZ - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $92.2
Premium cabin flights to Chicago
Premium cabin
2026-11-05
AUS - ORD
First | Non stop
From 32,500 Pts + $5.6
Premium cabin
2026-11-05
MDE - ORD
First | 2 Stops
From 33,000 Pts + $125.7
Premium cabin
2026-11-05
SEA - ORD
First | Non stop
From 40,500 Pts + $5.6
Premium cabin
2026-11-05
AUS - ORD
First | 1 Stop | 5 left
From 49,800 Pts + $5.6
Premium cabin
2026-11-05
NAS - ORD
First | 1 Stop | 3 left
From 75,000 Pts + $118.9
Premium cabin
2026-11-05
PTY - ORD
First | 1 Stop
From 95,500 Pts + $77.4
Flights departing from all over the world
Lexington, KY - Chicago
From 4,500 Pts + $25.6
Springfield, IL - Chicago
From 4,500 Pts + $25.6
Fayetteville, AR - Chicago
From 4,500 Pts + $25.6
Huntsville, AL - Chicago
From 4,500 Pts + $25.6
Wausau, WI - Chicago
From 4,500 Pts + $25.6
Champaign, IL - Chicago
From 4,500 Pts + $25.6
Washington, DC - Chicago
From 4,500 Pts + $25.6
Omaha, NE - Chicago
From 4,500 Pts + $25.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
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.
These are the hottest routes into Chicago right now, ranked by recent search activity on PointsYeah. Award space and fares change daily.
Flights New York - ChicagoFlights Washington - ChicagoFlights Atlanta - ChicagoFlights Tokyo - ChicagoFlights Boston - ChicagoFlights Minneapolis - ChicagoFlights Los Angeles - ChicagoFlights Paris - ChicagoFlights Detroit - ChicagoFlights London - ChicagoFlights Raleigh-durham - ChicagoFlights Seattle - ChicagoFlights Fort Lauderdale - ChicagoFlights Austin - ChicagoFlights San Francisco - ChicagoFlights Charlotte - ChicagoFlights Las Vegas - ChicagoFlights San Diego - ChicagoFlights New Orleans - ChicagoFlights Dallas-Fort Worth - ChicagoFlights Salt Lake City - ChicagoFlights Philadelphia - ChicagoFlights Toronto - ChicagoFlights Cancun - Chicago
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