The Windy City is a fantastic destination with an incredible diversity of things to see and do. However, one of the most fascinating aspects of Chicago is the dozens of different neighborhoods, each with its own unique feel and community, so I teamed up with to make planning your Chicago vacation just a bit easier. Depending on what you want to experience, there’s a wide variety of cool neighborhoods in Chicago to explore, so be sure to take your time and see as much as possible. To get you settled in, check out the many Chicago vacation rental options on Expedia.

Wicker Park

This neighborhood is definitely one of Chicago’s best. It’s also considered a very chic and hipster area because Wicker Park has numerous boutiques, unique restaurants with plenty of vegetarian options, and special donut shops. One of the best things to do here would be stroll down its relaxing tree-lined streets, only to end up shopping in one of its many niche shops.

Logan Square

Logan Square can be found just a few blocks northwest of Wicker Park, and this is an even more relaxed neighborhood. It’s an area in Chicago that attracts art lovers both old and young, as it’s a much less conforming neighborhood than the ones in the surrounding area. Although it attracts mostly young professionals and families, Logan Square attracts retired Chicago seniors as a great place to live. Logan Square is THE place to check out for all the best food-related endeavors, as it’s a neighborhood that features many chefs who seek to become experts in their fields. Besides amazing restaurants, you can also find awesome cocktail bars here.


A stunningly urban location, Pilsen features some of the best street art in Chicago. Merely walking along its streets you can discover a marvelous piece of street art in its many nooks and crannies. Besides some of the best Mexican food in the entire Midwest, here you can find the largest center of Mexican culture in the US – the National Museum of Mexican art. Also, don’t neglect to check out Thalia Hall, which is one of the finest places in the city for live music.


If you’re looking to discover a place that features the perfect blend of Old and New Chicago, then look no further than Uptown. It’s a very lively location with plenty of historic spots, as this neighborhood used to be the place where Charlie Chaplin himself produced his movies at Essanay Studios. That studio may be defunct now, but there are plenty of establishments from that era, like Al Capone’s favorite spot, the jazzy Green Mill. Also, make sure to see as much of the prominent Art Deco architecture as possible.


Although Chinatown in Chicago isn’t as large or iconic as its counterparts in New York and San Francisco, it’s still very much an amazing destination. You can easily get lost for an entire day here simply sampling its many unique eateries, as the dim sum options here are excellent. Make sure to stop by at the largest outdoors Chinese Mall in the Midwest, which is called Chinese Square. Another amazing thing to do here would be to catch a water taxi and experience the city from the river.

Chicago is always an exciting destination to visit. It has dozens of unique neighborhoods in which we just scratched the surface They’re important cultural parts of the city, and exploring them is always a treat. Have a great trip!