100%Nonstop
85Routes
7CA Airports
72Vetted hotels
129Trips this month
5 days away
True After-Work Departure147 viewed this week
Why we love this weekend
$322/night for Hotel 55 Chicago Downtown. Steep, but it puts you next to the things you actually came for instead of a mile from any of them. Walk the Riverwalk, take the L, and don't skip the architecture boat tour.
4.0-star property
Outbound to ChicagoFri, Jun 26
United$227
10:25 PM→4:36 AM
4h 11m · Nonstop
Return to SANSun, Jun 28
United$227
1:00 PM→3:25 PM
4h 25m · Nonstop
Hotels for this weekend
Three options in Chicago for Fri, Jun 26.
Our pick
Hotel 55 Chicago Downtown
8.8/10·4-star
$322/night
$644 for 2 nights
Luxury option
Trump International Hotel & Tower Chicago
9.4/10·5-star
$716/night
$1,432 for 2 nights
Budget option
Central Loop Hotel
8.6/10·4-star
$270/night
$540 for 2 nights
Estimated total
~$1,279
Flight + 2-night hotel
Before taxes & fees
Weekend Score
57?
Score
departure
85
return
80
price
0
duration
45
hotel
88
Prices are estimates. Final price on provider site. We may earn a commission.