100%Nonstop
63Routes
7CA Airports
72Vetted hotels
55Trips this month
Weekends in Chicago
Deep dish, jazz clubs, and the best architecture walk in America.
← All destinations
Top pick
4 days away
57?
Score
LAX → ORD · Fri, Jul 24
Top-Rated HotelTrue After-Work Departure
Fri 11:59 PM4h 18m · Nonstop
Sun 9:13 PM4h 44m · Nonstop
Hyatt Centric Chicago Magnificent Mile
9/10 · ★★★★ · ORD
169 viewed30 saved this week
Est. total
$1,843 flight + hotel
Before taxes & fees
4 days away
55?
Score
SAN → ORD · Fri, Jul 24
Top-Rated Hotel
Fri 4:41 PM4h 18m · Nonstop
Sun 4:05 PM4h 27m · Nonstop
Hyatt Centric Chicago Magnificent Mile
9/10 · ★★★★ · ORD
154 viewed28 saved this week
Est. total
$1,835 flight + hotel
Before taxes & fees
4 days away
52?
Score
SFO → ORD · Fri, Jul 24
Top-Rated Hotel
Fri 3:10 PM4h 28m · Nonstop
Sun 9:35 PM4h 57m · Nonstop
Hyatt Centric Chicago Magnificent Mile
9/10 · ★★★★ · ORD
136 viewed24 saved this week
Est. total
$2,074 flight + hotel
Before taxes & fees
Get next week's best weekends
Real deals. Friday departures. No spam — just weekends worth taking.