100%Nonstop
59Routes
7CA Airports
72Vetted hotels
55Trips 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 $1821. Best Weekend Score: 51/100.
Deep dish, jazz clubs, and the best architecture walk in America.
Top pick
2 days away
51?
Score
SAN → ORD · Fri, Sep 4
Fri 4:14 PM4h 6m · Nonstop
Sun 12:40 PM4h 22m · Nonstop
The Chicago Hotel Collection Ambassador Gold Coast
8/10 · ★★★★ · ORD
159 viewed29 saved this week
Est. total
$1,821 flight + hotel
Before taxes & fees
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