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
29 Nov 2026*RSNA Annual Meeting
Chicago, United StatesCongress13 Feb 2027*Chicago Auto Show
Chicago, United StatesTrade show15 May 2027*National Restaurant Association Show
Chicago, United StatesTrade show28 May 2027*ASCO Annual Meeting
Chicago, United StatesCongress5 Jun 2027*University of Chicago Convocation
Chicago, United StatesGraduation13 Jun 2027*Northwestern Commencement
Chicago, United StatesGraduation5 Aug 2027*Lollapalooza
Chicago, United StatesFestival8 Oct 2027Chicago Marathon
Chicago, United StatesMarathon11 Sept 2028*IMTS
Chicago, United StatesTrade show
Chicago, United StatesCongress13 Feb 2027*Chicago Auto Show
Chicago, United StatesTrade show15 May 2027*National Restaurant Association Show
Chicago, United StatesTrade show28 May 2027*ASCO Annual Meeting
Chicago, United StatesCongress5 Jun 2027*University of Chicago Convocation
Chicago, United StatesGraduation13 Jun 2027*Northwestern Commencement
Chicago, United StatesGraduation5 Aug 2027*Lollapalooza
Chicago, United StatesFestival8 Oct 2027Chicago Marathon
Chicago, United StatesMarathon11 Sept 2028*IMTS
Chicago, United StatesTrade show
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
| Budget | Where | Why |
|---|---|---|
| Budget | West Loop and South Loop | Near McCormick Place and the trains. |
| Mid-range | River North and the Loop | Walk to the river and Millennium Park. |
| Splurge | Magnificent Mile and Gold Coast | Grand hotels by the lake. |
Three hotels we would book
- Budget: Hotel Chicago West Loop
- Mid-range: Hotel Julian Chicago
- Splurge: The Peninsula Chicago
Tours
Half day · Low walking · Family
Chicago Architecture Center river cruise
The famous 90-minute river cruise.
Where to eat
With kids
- Field Museum.
- Shedd Aquarium.
- Museum of Science and Industry.
Rainy-day backups
- Art Institute.
- Field Museum.
Free things to do
- Millennium Park and the Bean.
- Lincoln Park Zoo.
- Lakefront Trail.
Getting around
- CTA L trains and buses take contactless. McCormick Place has a Metra station and the #3 bus.