HomeCHICAGO

Book Chicago tickets in May 2026

Most booked

Most booked in Chicago in May 2026

Chicago attractions

Iconic landmarks, museums and galleries — book entry tickets in advance to skip the line where supported.

Sort
View all attractions

Chicago tours

Guided walking tours, hop-on-hop-off buses and small-group experiences led by local guides.

Sort
View all tours

Curated

Chicago hidden gems

High-rated experiences that haven't gone viral (yet)

Calendar

What's on in Chicago

Browse by month — what's happening in Chicago this month, next month and beyond.

  • Official venue tickets

    Direct from the venue

  • Secure payment

    Powered by Stripe

  • Refund guarantee

    If your event is cancelled

  • Exclusive discounts

    Free with tickadoo+ membership

tickadoo+

Save up to 15% on every Chicago booking

Free to join. 5% off your first booking, 10% off your second, 15% off every booking after.

Join free

Chicago · May 2026

Chicago in May 2026

Long daylight, warmer evenings, and Chelsea Flower Show. Garden tours at Kew and Hampton Court come into their own. 75 experiences in Chicago are confirmed bookable in May 2026 — book ahead for the best seats at West End theatre shows and flagship attractions.

Top picks for May 2026: Go City Chicago All-Inclusive Pass: Pilih dari 39 Atraksi, Skydeck Chicago: Entry Ticket, and The Art Institute of Chicago: Fast Pass.

Average rating across these Chicago experiences sits at 3.0 stars.

Before you book

Frequently asked questions

Answers to the most common questions about booking experiences in Chicago.

Go City Chicago All-Inclusive Pass: Pilih dari 39 Atraksi, Skydeck Chicago: Entry Ticket, and The Art Institute of Chicago: Fast Pass lead the line-up. 75 experiences in total across West End theatre, attractions, tours and Thames cruises.

From the tickadoo blog

Read more about Chicago

Hand-picked travel guides, show reviews, and itineraries — all free, all written by our editorial team.