Chicago skyline
MDW
Chicago
Boston skyline and harbor
BOS
Boston

Chicago → Boston

Southwest Airlines · Round Trip · Nonstop

$166

per person · round trip

Book This Deal

Flight Details

Cabin
Economy
Departs
May 4, 2026
Returns
May 10, 2026

Planning your trip to Boston?

Complete your trip with these deals.

Hotels in Boston

Find the best hotel deals for your stay.

Explore →

Rental Cars in Boston

Get around with affordable rental car deals.

Explore →

Adventures in Boston

Explore tours, activities, and experiences.

Explore →
Round Trip Chicago to Boston - $166 on Southwest Airlines | Woven Adventures