Events from 2nd Oct 2026 to 3rd Oct 2026

★Local Picks & Special Events

Fri 2nd Oct 2026

★ Candlelight: Tribute to Juan Gabriel on Strings

Immerse yourself in the magic of live music at the Candlelight: Tribute to Juan Gabriel on Strings event at the historic Stan Mansion in Chicago. This unique concert series offers a multi-sensory expe

Sat 3rd

Oct

Sat 3rd Oct 2026

★ Pure Prairie League

music

Get ready to experience a night of timeless country rock classics with Pure Prairie League at the iconic Arcada Theatre in Chicago. Known for hits like 'Amie' and 'Falling In and Out of Love,' Pure Pr

All Events 2nd Oct 2026 - 3rd Oct 2026

Fri 2nd

Oct

Fri 2nd Oct 2026

Candlelight: Tribute to Juan Gabriel on Strings

music

Chicago River: 1.5-Hour Guided Architecture Cruise

Friday 2

October

Friday 2 October 2026

Chicago River: 1.5-Hour Guided Architecture Cruise

Event

HighlightsPre-purchase your ticket to skip the ticket line and guarantee your place on this popular cruiseExperience the architectural river tour which started it all – back in 1935Enjoy year-long c

45-Minute Family-Friendly Architecture River Cruise

Friday 2

October

Friday 2 October 2026

45-Minute Family-Friendly Architecture River Cruise

Event

HighlightsNavigate with your family through the heart of the City on the Chicago RiverLearn from expert guides about what makes Chicago architecture so amazingRelax on board with locally sourced food

Chicago Explorer Pass: 2 to 7 Attractions including SkyDeck

Friday 2

October

Friday 2 October 2026

Chicago Explorer Pass: 2 to 7 Attractions including SkyDeck

Event

HighlightsSave up to 50%* off combined admission prices at top Chicago attractionsPick your favorite 2, 3, 4, 5, 6 or 7 things to do over 30 daysTake a trip up the iconic Willis Tower for Skydeck Chic

Gangsters and Ghosts Guided Walking Tour

Friday 2

October

Friday 2 October 2026

Gangsters and Ghosts Guided Walking Tour

Event

HighlightsLearn about the dark history of Chicago's South Loop from a historian guideHear true tales of Chicago's gangster past and learn how Al Capone ran his empireListen to eerie tales of ghosts th

Friday 2

October

Friday 2 October 2026

Mob and Crime Bus Tour

Event

HighlightsSee the world famous St. Valentine's Day massacre siteWalk the final steps of John Dillinger, Chicago's most famous bank robberAdmire the city’s spectacular architecture and Prohibition Er

1-5 Day Attraction Pass with Shedd Aquarium

Friday 2

October

Friday 2 October 2026

1-5 Day Attraction Pass with Shedd Aquarium

Event

HighlightsSave up to 50%* at top Chicago attractions with one single passChoose from a 1, 2, 3 or 5-days pass and explore over 35 things to doEnjoy birds-eye views from the top of SkyDeck Chicago and

Friday 2

October

Friday 2 October 2026

Bikes, Bites, and Brews Biking Tour

Event

HighlightsStop at one of Chicago's best known pizza jointsTry a delicious brownie in the city that invented itLearn the only way you can make a hot dog in ChicagoOn the daytime version of the tour, ri

Chicago Night Driving Tour with Skydeck and River Cruise

Friday 2

October

Friday 2 October 2026

Chicago Night Driving Tour with Skydeck and River Cruise

Event

HighlightsSkydeck Admission (Admission Included)Chicago Shorline Cruise (Admission Included)Complimentary Hotel Pick-Up and Drop-Off in Downtown ChicagoSmall Group Narrated Driving Tour (Max 6 People)

Friday 2

October

Friday 2 October 2026

Taste of Chinatown Food Walking Tour

Event

HighlightsTaste authentic food from several distinct regions of ChinaMarvel at the incredible culture of the Chinese peopleLearn about the vibrant history of Chicago's ChinatownLocal commentary and hi

Friday 2

October

Friday 2 October 2026

360 CHICAGO Observation Deck Ticket

Event

HighlightsExperience the best aerial view of the heart of Chicago and the Magnificent MileEnjoy the convenience of skipping the ticket purchase process at 360 ChicagoZoom up 1,000 feet in just 40 seco

Not quite what you’re looking for yet?

Use filters to narrow things down or explore other categories.

Refine filters

We Are Part of the My Guide Network!

My Guide Chicago is part of the global My Guide Network of Online & Mobile travel guides. We are now in 180+ Destinations and Growing.

Nearby Destinations

Events from 2nd Oct 2026 to 3rd Oct 2026

★Local Picks & Special Events

★ Candlelight: Tribute to Juan Gabriel on Strings

★ Pure Prairie League

All Events 2nd Oct 2026 - 3rd Oct 2026

Candlelight: Tribute to Juan Gabriel on Strings

Chicago River: 1.5-Hour Guided Architecture Cruise

45-Minute Family-Friendly Architecture River Cruise

Chicago Explorer Pass: 2 to 7 Attractions including SkyDeck

Gangsters and Ghosts Guided Walking Tour

Mob and Crime Bus Tour

1-5 Day Attraction Pass with Shedd Aquarium

Bikes, Bites, and Brews Biking Tour

Chicago Night Driving Tour with Skydeck and River Cruise

Taste of Chinatown Food Walking Tour

360 CHICAGO Observation Deck Ticket

Not quite what you’re looking for yet?

We Are Part of the My Guide Network!

Nearby Destinations

Discover More

For Businesses

Events from 2nd Oct 2026 to 3rd Oct 2026

★Local Picks & Special Events

★ Candlelight: Tribute to Juan Gabriel on Strings

★ Pure Prairie League

All Events 2nd Oct 2026 - 3rd Oct 2026

Candlelight: Tribute to Juan Gabriel on Strings

Chicago River: 1.5-Hour Guided Architecture Cruise

45-Minute Family-Friendly Architecture River Cruise

Chicago Explorer Pass: 2 to 7 Attractions including SkyDeck

Get your event seen

Gangsters and Ghosts Guided Walking Tour

Mob and Crime Bus Tour

1-5 Day Attraction Pass with Shedd Aquarium

Bikes, Bites, and Brews Biking Tour

Chicago Night Driving Tour with Skydeck and River Cruise

Taste of Chinatown Food Walking Tour

360 CHICAGO Observation Deck Ticket

Not quite what you’re looking for yet?

We Are Part of the My Guide Network!

Nearby Destinations