Cheap Flights from Chicago to Boston
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, cabin, and date, but available award flights can start around 7,500 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 from Chicago to Boston for specific travel dates.
2026-11-07
ORD - BOS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-08
ORD - BOS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-09
ORD - BOS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
ORD - BOS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-11
ORD - BOS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-12
ORD - BOS
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to Boston flight facts
Distance
868 mi
1,398 km in a straight line
Estimated flight time
about 2h 15m
In the air, for the straight-line distance
Time difference
+1h
Boston is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Boston
BOS · General Edward Lawrence Logan Intl
Nearby airport alternatives
Flights Chicago - Manchester NH · Manchester NH is 45 mi from Boston
Flights Chicago - Worcester · Worcester is 45 mi from Boston
Flights Chicago - Providence · Providence is 49 mi from Boston
Flights Milwaukee - Boston · Milwaukee is 73 mi from Chicago
Flights South Bend - Boston · South Bend is 86 mi from Chicago
Flights Chicago - Windsor Locks · Windsor Locks is 91 mi from Boston
Premium cabin flights from Chicago to Boston
Premium cabin
2026-11-05
ORD - BOS
First | 1 Stop | 5 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-06
ORD - BOS
First | 1 Stop | 7 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-06
ORD - BOS
First | Non stop | 1 left
From 27,600 Pts + $5.6
Premium cabin
2026-11-07
ORD - BOS
First | Non stop | 4 left
From 27,600 Pts + $5.6
Premium cabin
2026-11-05
ORD - BOS
First | Non stop
From 30,000 Pts + $5.6
Premium cabin
2026-11-07
ORD - BOS
First | Non stop
From 30,000 Pts + $5.6
Selected hotels for your next stay
Falmouth, MA (USA)
AutoCamp Cape Cod
From 74,000 Pts or $173
Boston, MA (USA)
The Westin Boston Seaport District
From Pts or $126
Boston, MA (USA)
The Ritz-Carlton, Boston
From Pts or $412
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.
Chicago and Boston are about 868 miles (1,398 km) apart in a straight line.
Flying the 868-mile straight-line distance takes about 2h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Boston is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Boston: General Edward Lawrence Logan Intl (BOS).
Travelers searching this route also look at other popular routes into Boston, plus the return trip when we track it. Fares and award space change daily.
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points travel planning experience. Yeah!
