This big city of 77 different neighborhoods has a surprisingly homey feel, with tons of attractions, incredible eats, and neighborhoods bursting with personality. Chicago has been voted the best big city in America for five years running, and rightfully so — there’s so much to do in the Windy City. Yes, even during those blustery winter months. Always wear your walking shoes in Chicago, there are plenty of places to pop in, like free museums and bars with a view as you wander around the city.

Award-winning dining (not just deep dish)

This city is so big that there are great restaurants on every block — the hardest part is narrowing down those endless options. Chicago is also home to a lot of Top Chef alums. Coincidence? We think not. From Italian to barbecue, budget-friendly to Michelin-rated restaurants, Chicago has you covered. Plus, it’s a magnet for post-college 20-somethings, so there are tons of trendy spots to eat and drink while surrounded by some amazing atmosphere and upbeat crowds.

Endless events

No matter the season, there’s always something on the city’s schedule. From street fairs to music festivals, Chicago buzzes with energy, year-round. This melting pot of communities is always celebrating its diverse array of people, from food and music to art, history, and culture. From November to January, this city is decked in the holiday spirit — bundle up and head out to gawk at the wonderland of twinkling lights, carolers, ice skating, and holiday markets. In warmer months, celebrate the fresh spring air with flower shows, fireworks, wine fests, and music of every genre. Oh, and there’s even a bacon fest.

Architecture and adventure

Home to the very first skyscrapers, Chicago is full of amazing monuments, landmarks, and other famous historic treasures. From walking tours to boat cruises along Lake Michigan, you’ll be craning your neck to catch a glimpse of all the mesmerizing architecture, hundreds of stories in the sky. Chicago is known as the “city in the garden,” especially during warmer months, because there’s so much green despite being a massive metropolitan city. Walk along trails and through parks to better see the intricate array of Chicago skyline around you.

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