Depart Boston on Friday March 16 at 6:30 pm. on JetBlue. Arrive Seattle at 9:45 pm.
Things to do in Seattle:
Seattle Central Library
Fremont Troll and Lenin
Bus Tunnel
Uwajimaya
Gas Works Park
Ivars Salmon House $$ Smith Tower Observation Deck $6
Obvious:
Space Needle nearsunset Monorail
Experience Music Project (at least the fence)
Pikes Market
Experience Music Project
Olympic Sculpture Park
Arrive Seattle at 9:45 pm.
Then

Depart Seattle on Monday March 19 @ 4:45 pm on the Empire Builder
Arrive Chicago on Wednesday March 21 @ 3:55 pm. - $241 per person (Student Advantage $219.50 per person (assuming 2 people))

Things to do in Chicago:
Ambassador East Hotel Location
Chicago Historical Society
Architecture Walking Tours
Judy Istock Butterfly Haven - Thursdays – FREE

Depart Chicago on Saturday March 24 @ 7:55 pm on the Lake Shore Limited
Arrive Boston on Sunday March 25 @ 6:30 pm - $183 per person (Student Advantage $171.00 per person (assuming 2 people))

Rail Fare: $424

Airfare:
Nonstop on Alaska - $169
Nonstop on Jet Blue - $184
1 Stop on United - $172

If we travel 2 weeks earlier, we can save $200 dollars. Total railfare, with AAA discount and H644, $575.40 for 2 people ($287.7 per person).