Chicago event weekends: what to do between sessions

Architecture on the river, deep-dish pizza, blues clubs and the lakefront, host of a marathon major, Lollapalooza and huge medical congresses.

Events we cover in Chicago

Arriving

O'Hare (ORD) has the CTA Blue Line to the Loop in 45 minutes; Midway (MDW) has the Orange Line in 25 minutes.

Where to stay

BudgetWhereWhy
BudgetWest Loop and South LoopNear McCormick Place and the trains.
Mid-rangeRiver North and the LoopWalk to the river and Millennium Park.
SplurgeMagnificent Mile and Gold CoastGrand hotels by the lake.

Three hotels we would book

Event weekends sell out early and prices rise as the date gets closer: book a cancellable room as soon as you know you are going.

Tours

Half day · Low walking · Family

Chicago Architecture Center river cruise

The famous 90-minute river cruise.

Half day · Food

Deep-dish pizza and food tour

Pizza, Italian beef and hot dogs.

Half day · Family · Indoor

Skydeck at Willis Tower

Glass ledge 103 floors up.

Evening · Nightlife

Blues club night

Live blues in the city that electrified it.

Evening · Low walking · Nightlife

Lake Michigan sunset cruise

Skyline from the lake.

Evening · Nightlife

Gangsters and ghosts tour

Prohibition history.

Half day · Family

Bike tour of the lakefront

Lakefront trail and parks.

Half day · Indoor · Low walking

Art Institute of Chicago

World-class collection.

Where to eat

With kids

Rainy-day backups

Free things to do

Getting around