Chicago Weekend

SFO → ORD · Fri, Jun 26 · 2 nights

5 days away

True After-Work Departure145 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$310

10:38 PM→5:01 AM

4h 23m · Nonstop

Return to SFOSun, Jun 28

United$310

9:35 PM→12:32 AM

4h 57m · 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

~$1,445

Flight + 2-night hotel

Before taxes & fees

Weekend Score

56?

Score

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Prices are estimates. Final price on provider site. We may earn a commission.