100%Nonstop
62Routes
7CA Airports
72Vetted hotels
57Trips this month
Tomorrow
Top-Rated Hotel142 viewed this week
Why we love this weekend
Trump International Hotel & Tower Chicago at $908/night isn't cheap, but for 36 hours in Chicago, the right hotel changes the whole shape of the trip. There's a pool, which is always a nice surprise for a weekend stay. Deep dish at Lou Malnati's, the architecture boat tour, jazz at Green Mill.
Pool on-site
5.0-star property
Outbound to ChicagoFri, Jun 5
United$266
3:00 PM→9:28 PM
4h 28m · Nonstop
Return to SFOSun, Jun 7
United$386
12:45 PM→3:28 PM
4h 43m · Nonstop
Hotels for this weekend
Three options in Chicago for Fri, Jun 5.
Our pick
Trump International Hotel & Tower Chicago
9.6/10·5-star
$908/night
$1,816 for 2 nights
Luxury option
The Langham, Chicago
9.8/10·5-star
$1,450/night
$2,900 for 2 nights
Budget option
Hilton Garden Inn Chicago Central Loop
9.2/10·3-star
$598/night
$1,196 for 2 nights
Estimated total
~$2,811
Flight + 2-night hotel
Before taxes & fees
Weekend Score
54?
Score
departure
60
return
80
price
0
duration
45
hotel
96
Prices are estimates. Final price on provider site. We may earn a commission.