100%Nonstop
61Routes
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 United, paired with vetted hotels, starting from $1351. Best Weekend Score: 54/100.
Deep dish, jazz clubs, and the best architecture walk in America.
Top pick
4 days away
54?
Score
SAN → ORD · Fri, Aug 28
Top-Rated Hotel
Fri 4:08 PM4h 6m · Nonstop
Sun 12:40 PM4h 22m · Nonstop
Arlo Chicago
9.4/10 · ★★★★ · ORD
164 viewed30 saved this week
Est. total
$1,351 flight + hotel
Before taxes & fees
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