Chicago

Chicago travel guide essentials? Iconic skyline, legendary eats, and enough museums, music, and neighborhood flavor to fill a dozen trips.

This Windy City blends world-class culture with Midwestern charm—and our guide makes it easy to dive right in.

Whether you’re chasing art, architecture, or the perfect slice of pizza, we’ll help you hit the ground running.

Articles

Our Chicago articles are built for real travelers—not just guidebook readers.

Plan your trip with themed itineraries like “48 Hours in Chicago,” “Where to Eat Near Millennium Park,” and “Free Things That Don’t Feel Budget.”

We break down the must-dos, local faves, and how to avoid the tourist traps (unless you’re into that).

Expect clickable maps, local-approved picks, and smart seasonal tips.

Events

Chicago events bring serious energy to the city—think Taste of Chicago, Lollapalooza, and a summer’s worth of rooftop parties and street fests.

Spring kicks off with flower shows and food markets, while fall delivers art fairs, harvest events, and Halloween that’s more stylish than spooky.

Winter sparkles with holiday lights and deep-dish-fueled pop-ups.

Our event guides make it easy to plan around the best of it.

Attractions

Chicago’s attractions got major range.

Stand under T. rex fossils at the Field Museum, walk through immersive art at the Art Institute, or ride the Ferris wheel on Navy Pier.

Cruise the Chicago River, bike the lakefront, or wander through Lincoln Park Zoo (spoiler: it’s free).

We cover iconic spots and lesser-known gems to balance your itinerary.

Shows

The theater scene in Chicago is bold, witty, and always worth a ticket.

Catch Second City comedy, see a Broadway tour, or find live jazz in a basement bar that feels like a secret.

Our guides help you score tickets, find the right vibe, and pair the show with dinner or late-night drinks.

Hotels

Chicago hotels serve up options—from sleek downtown towers to boutique hideaways tucked into neighborhood streets.

Want skyline views? Easy museum access? Close to nightlife? We’ve sorted it.

Expect deals, perks, and pro tips for the best places to crash after your day in the city.

Packages

Our Chicago travel packages bundle top attractions, shows, and hotels into easy, ready-to-go deals.

Whether you’re visiting for a weekend or turning it into a weeklong adventure, we help you make the most of your stay.

Let your Chicago travel guide do the heavy lifting—so you can spend your time soaking up the city’s best.

You can also check out our full list of destinations here for more travel tips!