Cheap Flights from Houston to Chicago
Looking for cheap flights from Houston to Chicago? 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 Houston to Chicago vary by season and date, but economy flights can start around 13,000–15,000 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 Houston to Chicago for specific travel dates.
2026-05-02
IAH - ORD
Economy | Non stop
From 13,800 Pts + $5.6
2026-05-02
IAH - ORD
Economy | Non stop | 9+ left
From 15,000 Pts + $34.2
2026-05-02
IAH - ORD
Economy | Non stop | 9+ left
From 15,000 Pts + $5.6
2026-05-02
IAH - ORD
Economy | Non stop
From 13,000 Pts + $5.6
2026-05-02
IAH - ORD
Economy | Non stop | 9+ left
From 15,000 Pts + $5.6
2026-05-02
IAH - ORD
Economy | Non stop | 9+ left
From 15,000 Pts + $34.1
Premium cabin flights from Houston to Chicago
Premium cabin
2026-05-02
IAH - ORD
First | Non stop | 2 left
From 30,000 Pts + $5.6
Premium cabin
2026-05-02
IAH - ORD
Business | Non stop
From 29,000 Pts + $5.6
Premium cabin
2026-05-02
IAH - ORD
First | Non stop
From 24,000 Pts + $5.6
Premium cabin
2026-05-02
IAH - ORD
First | Non stop | 2 left
From 30,000 Pts + $5.6
Premium cabin
2026-05-02
IAH - ORD
Business | Non stop | 2 left
From 30,000 Pts + $34.1
Premium cabin
2026-05-02
IAH - ORD
Business | Non stop | 2 left
From 30,000 Pts + $34.2
Selected hotels for your next stay
Chicago (United States)
Thompson Chicago
From 17,000 Pts or $202
Vernon Hills (United States)
Hotel Indigo Chicago-Vernon Hills
From 18,000 Pts or $126
Chicago (United States)
Park Hyatt Chicago
From 21,000 Pts or $537
Frequently Asked Questions
The cheapest route from Houston to Chicago 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 Houston to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Houston to Chicago.
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Our mission is to provide the simplest and best
points travel planning experience. Yeah!
