Shared Itinerary

The Ultimate Chicago Weekend

A curated 3-day itinerary covering the best sights, sounds, and tastes in Chicago.

S
Staynxplore Admin 11 items Jul 31 – Aug 2, 2026 3 days

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1

Day 1 Friday, Jul 31

Reggie's Music Joint

Reggie's Music Joint

Chicago · 2105 S State St.
Reggie's Rock Club

Reggie's Rock Club

Chicago · 2109 S. State St.
2

Day 2 Saturday, Aug 1

Millennium Park Welcome Center

Millennium Park Welcome Center

Chicago · 201 E Randolph St
The Congress Plaza Hotel & Convention Center

The Congress Plaza Hotel & Convention Center

Chicago · 520 S Michigan Ave
3

Day 3 Sunday, Aug 2

540 N Lake Shore Dr

540 N Lake Shore Dr

Chicago · 540 N Lake Shore Dr
425 S Financial Pl

425 S Financial Pl

Chicago · 425 S Financial Pl

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