100%Nonstop
62Routes
7CA Airports
72Vetted hotels
57Trips this month
Weekend trips from San Diego to Chicago
1 weekend packages from San Diego (SAN) to Chicago (ORD). Nonstop flights on American, paired with vetted hotels, starting from $2567. Best Weekend Score: 58/100.
Deep dish, jazz clubs, and the best architecture walk in America.
Top pick
2 days away
58?
Score
SAN → ORD · Fri, Jun 5
Top-Rated HotelTrue After-Work Departure
Fri 10:45 PM4h 26m · Nonstop
Sun 7:59 PM4h 37m · Nonstop
Trump International Hotel & Tower Chicago
9.6/10 · ★★★★★ · ORD
171 viewed31 saved this week
Est. total
$2,567 flight + hotel
Before taxes & fees
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