Cheap Flights from Chicago to Boston
Looking for cheap flights from Chicago to Boston? 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 Boston vary by season and date, but economy flights can start around 7,500–25,000 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 Chicago to Boston for specific travel dates.
2026-04-22
ORD - BOS
Economy | Non stop
From 16,000 Pts + $5.6
2026-04-22
ORD - BOS
Economy | 1 Stop | 9+ left
From 17,600 Pts + $30.6
2026-04-22
ORD - BOS
Economy | 1 Stop | 9+ left
From 25,000 Pts + $5.6
2026-04-22
ORD - BOS
Economy | Non stop | 9+ left
From 7,500 Pts + $18.1
2026-04-22
ORD - BOS
Economy | 1 Stop | 9+ left
From 12,500 Pts + $14.7
2026-04-22
ORD - BOS
Economy | Non stop
From 13,800 Pts + $5.6
Premium cabin flights from Chicago to Boston
Premium cabin
2026-04-22
ORD - BOS
Business | 1 Stop | 1 left
From 28,000 Pts + $121.4
Premium cabin
2026-04-22
ORD - BOS
Business | Non stop
From 29,000 Pts + $5.6
Premium cabin
2026-04-22
ORD - BOS
First | Non stop | 9+ left
From 30,000 Pts + $5.7
Premium cabin
2026-04-22
ORD - BOS
First | Non stop | 7 left
From 39,400 Pts + $5.6
Premium cabin
2026-04-22
ORD - BOS
First | Non stop
From 32,500 Pts + $5.6
Premium cabin
2026-04-22
ORD - BOS
First | Non stop | 7 left
From 15,000 Pts + $18.1
Selected hotels for your next stay
Cambridge (United States)
Kimpton Marlowe Hotel
From 36,000 Pts or $221
Falmouth, MA (USA)
AutoCamp Cape Cod
From 52,000 Pts or $98
Somerville, MA (USA)
The Row Hotel at Assembly Row, Autograph Collection
From Pts or $253
Frequently Asked Questions
The cheapest route from Chicago to Boston 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 Boston.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Boston.
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points travel planning experience. Yeah!
