Chicago Travel Guide 2026

Chicago Holidays

Chicago’s holidays. One easy place to plan them.

Free events, markets, lights and shows across the city and suburbs. Filter by budget, date and neighborhood, then save your plan on your phone.

As Seen On FOX 32 Chicago WGN FOX 17 West Michigan WDIV Detroit FOX 2 Detroit

Merry Chicago · Free

Your holiday plan in three steps.

  1. Filter by free admission, family-friendly, date night or this weekend.
  2. Switch between city and suburbs, then open an event for its dates, hours and official site.
  3. Save it to My List, and add Merry Chicago to your phone’s home screen.

No account and no app-store download. Dog-friendly and accessibility details appear where organizers confirm them. Sponsored listings are always labeled.

Open Merry Chicago →
Cloud Gate the Bean reflecting the Chicago skyline at sunset Editor’s Pick

Weekend Guide

The Perfect Chicago Weekend

Two days, three meals, one skyline view you won’t forget — the itinerary I’d hand a friend on their first visit.

Read the guide →

Explore Chicago By Neighborhood

Chicago is really a collection of neighborhoods, each with its own personality — and the best way to find your kind of trip is to start with the map. Tap any neighborhood to dig into where to eat, drink, and explore, from Andersonville up north to Pilsen and the South Loop.

Holiday guides

Tree lightings, markets, trains and New Year’s Eve.

Read the local guides for the story behind each tradition, then use Merry Chicago to find dates and plan the day.

We Map the Best of Chicago

We don’t just list Chicago’s best spots — we pin them. Many of our guides come with a map, so you can find what’s nearest you or your hotel instead of scrolling a list. Our rooftop bar map is a good place to start: skyline lounges downtown, local beer gardens up north, each pinned and ready to explore.

Map of the best rooftop bars in Chicago showing locations across Lincoln Square, River North, the Loop, and Lincoln Park
Jill Halpin, Chicago travel expert and founder of Little Chicago Guide

Hi, I’m your guide

Chicago is my second home, and my favorite story to tell.

I split my time between Chicago and Michigan, and I’ve talked Chicago travel on FOX 32, WGN and FOX 17 West Michigan. Little Chicago Guide is what I’d tell a friend before their first visit: neighborhood favorites, honest restaurant picks, and the parts of the city that aren’t on the postcards. Sponsored listings are always labeled.

About the guide →

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