100%Nonstop
38Routes
7CA Airports
69Vetted hotels
31Trips this month
Weekend trips from San Francisco to Chicago
1 weekend packages from San Francisco (SFO) to Chicago (ORD). Nonstop flights on United, paired with vetted hotels, starting from $1748. Best Weekend Score: 53/100.
Deep dish, jazz clubs, and the best architecture walk in America.
Top pick
6 days away
53?
Score
SFO → ORD · Fri, Oct 23
Top-Rated Hotel
Fri 3:00 PM4h 37m · Nonstop
Sun 8:29 PM4h 59m · Nonstop
The Royal Sonesta Chicago Downtown
9.4/10 · ★★★★ · ORD
162 viewed29 saved this week
Est. total
$1,748 flight + hotel
Before taxes & fees
Get next week's best weekends
Real deals. Friday departures. No spam — just weekends worth taking.