For those based in the Bay Area. Grueling 6669 total miles.
Several dates open. Ex:

San Jose (SJC) to Boston (BOS) - Tue, Nov 5open

United Airlines, Inc. 366 Dep: 6:20AM Arr: 12:04PM 3h 44m Airbus A319 Coach (N)
Layover in IAH 3h 26m
United Airlines, Inc. 682 Dep: 3:30PM Arr: 6:11PM 2h 41m Airbus A319 Coach (N)
Layover in ORD 3h 13m
United Airlines, Inc. 1242 Dep: 9:24PM Arr: 12:42AM 2h 18m Boeing 737 Coach (N)
Wed, Nov 6
--------------------------------------------------------------------------------

Boston (BOS) to San Jose (SJC) - Wed, Nov 6

United Airlines, Inc. 1020 Dep: 9:00AM Arr: 12:29PM 4h 29m Boeing 737 Coach (N)
Layover in IAH 1h 16m
United Airlines, Inc. 212 Dep: 1:45PM Arr: 3:30PM 3h 45m Boeing 757 Coach (N)
Layover in LAX 38m
United Airlines, Inc. 6519 Dep: 4:08PM Arr: 5:25PM 1h 17m Canadair RJ 700 Coach (N)
OPERATED BY SKYWEST DBA UNITED EXPRESS


FARE AND BOOKING DETAILS

Provide this information to a travel agent to help them match the fares found.
Make sure to provide the exact booking and fare codes shown.

Fare 1: Carrier UA NA21KN SJC to BOS $94.88
Passenger type ADT, one-way fare, booking code N
Covers SJC-IAH (Economy), IAH-ORD (Economy), ORD-BOS (Economy)

Fare 2: Carrier UA NA21KN BOS to SJC $94.88
Passenger type ADT, one-way fare, booking code N
Covers BOS-IAH (Economy), IAH-LAX (Economy), LAX-SJC (Economy)

US Transportation Tax (US) $14.24
US September 11th Security Fee (AY) $10.00
US Passenger Facility Charge (XF) $15.00
US Flight Segment Tax (ZP) $23.40

Subtotal per passenger $252.40
Number of passengers x1

Total airfare & taxes $252.40