Visit the Windy City: Plan a Chicago Vacation

While there are fine accommodations throughout the city, where to stay in Chicago depends on the purpose of your trip. If you're visiting to watch baseball at Wrigley Field, consider looking for lodging in the Lakeview neighborhood. Are you more interested in Chicago’s famed museums and outdoor activities? Accommodations close to Hyde Park will be great options for you. Look for AAA Diamond designations when searching for the best hotels in Chicago.

Once you have arrived, navigating the Windy City is a breeze. Driving and finding parking in busy areas can be challenging, but getting around Chicago without a car is easy. As a thriving metropolis, you can get to many places on foot. Even better, public transit in Chicago is fast and reliable, and you can take advantage of the rideshare and bikeshare programs available throughout the city. You can even take a water taxi!

With spectacular cuisine, sports, comedy and culture everywhere you look, Chi-Town is always a lively locale, so do not worry about spending too long there. Three to five days gives you enough time to see the sights and participate in some popular Chicago activities. However, if you want to get acquainted with the city, give yourself at least a week to explore. When planning your itinerary, include some of the best Chicago museums.

Gorgeous architecture, world-class sports and performance arts, fascinating history, fine dining and thrilling nightlife are just some of the things Chicago has to offer. There are plenty of must-see sights for even the most discerning traveler. Stroll around one of the Windy City’s beautiful parks or catch some rays at one of Chicago’s beaches on the shore of Lake Michigan. Catch an improv show or see some of the renowned Chicago museums. Whatever your pleasure, the Illinois gem is surely worth a visit.

Although it is known as the Windy City, the climate is rather pleasant most of the year. Weather in Chicago ranges from mild summer days in the 70s and 80s to chilly winter days below 32ºF, but the action never stops. Depending on your preferences, the best time to visit Chicago might be January to save on expenses and avoid crowds or July to enjoy outdoor Chicago attractions.

Chicago is not just a place for big business meetings and nights on the town. It is also a hotspot for family visitors, with museums, activities, parks and art galore. Some popular ideas for things to do in Chicago with kids are riding the Ferris wheel at Navy Pier, catching a Bulls or Cubs game, visiting the Lincoln Park Zoo or seeking thrills just north of the city at Six Flags Great America.

The Windy City is known worldwide as a hub for incredible eats, but what are the mandatory munchies? Perhaps the most iconic Chicago food is the buttery, deep-dish pizza found at restaurants throughout the city, but other top things to eat in Chicago include the Italian Beef Sandwich, deep-dish pizza and, of course, the legendary Chicago Dog.