Chicago itineraries
The Loop in a Day, River and Sky
First time, one day? Stay inside the Loop. Pancakes first, then the Bean and the Art Institute, a deep-dish wait, a boat ride between the towers, and the glass box on Willis Tower at sunset.
Lakefront Museums and the North Side
One day on the lakefront Museum Campus and the Loop, one day north from the Mag Mile to Lincoln Park and Navy Pier. Sleep in River North and everything is a walk or one bus away.
Loop, South Side, North Side
Day one the Loop and West Loop restaurants, day two Hyde Park's science museum and Chinatown, day three Wicker Park, Wrigley and jazz at the Green Mill. Three directions, into the neighbourhoods. Base in the Loop.
Festivals & seasons
- 1 — Deep winter: sub-zero wind, cheapest hotels
- 3 — St. Patrick's Day: the river turns green
- 5 — May and September: the best walking weather
- 6 — Chicago Blues Festival
- 6 — Chicago Pride Parade
- 7 — Taste of Chicago
- 7 — High summer: hot, humid, peak season
- 7 — Lollapalooza
- 8 — Chicago Air and Water Show
- 9 — Chicago Jazz Festival
- 10 — Chicago Marathon & Open House Chicago
- 11 — Christkindlmarket & Thanksgiving Parade
Souvenirs
- Garrett Popcorn Chicago Mix tin
- Frango mint chocolates
- Cubs cap and ivy-wall gear
- Art Institute prints and magnets
- Skyline books and building models
- Intelligentsia coffee beans
- Wicker Park vinyl
- Christkindlmarket boot mug