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.

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    Merry Chicago · Free holiday app

    Chicago for the holidays, at your fingertips.

    Lights, markets, shows, Santa, holiday teas and free events across the city and suburbs. Filter by free, family-friendly or date night, save your list, add it to your calendar. No account, no app-store download.

    Open Merry Chicago →
    Merry Chicago, the Chicago holiday app, open on a phone held in a hand
    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 →
    Illustrated Chicago neighborhood map with the Little Chicago Guide logo Andersonville Lincoln Square Ravenswood Uptown Lakeview & Wrigleyville Logan Square Bucktown Lincoln Park Wicker Park Old Town Gold Coast Fulton Market River North & Mag Mile Streeterville West Loop The Loop Pilsen South Loop Hyde Park

    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.

    See All Neighborhoods →

    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.

    Start here

    New to Chicago? Start here.

    Six guides to read first, whether you’re visiting for a weekend or just signed a lease.

    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.

    Explore the Rooftop Map →
    Map of the best rooftop bars in Chicago showing locations across Lincoln Square, River North, the Loop, and Lincoln Park

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