Chicago has so much energy, culture, incredible architecture, and, of course, deep-dish pizzas. If anything, we’d just go there for the pizza and have one for breakfast, lunch, and dinner.
Known as the Windy City mainly because of the chilly breezes off Lake Michigan (we won’t get into the political meaning), the vibe here is just off the charts.
But we will say that if you’re thinking about going for an extended stay, stay outside of the chaos and crazy prices of the downtown area. Below are some of the better neighborhood options.
The Best Neighborhoods to Stay in Chicago
While a quick weekend getaway might lead you straight to a commercial hotel on the Magnificent Mile, an extended exploration of the city’s rich neighborhoods demands a more authentic home base. For families, groups, or remote workers planning a longer stay, finding an accommodation that offers separate living spaces and home-like amenities is essential.
Exploring the diverse market of short-term rentals in Chicago via a comprehensive meta-search tool like Cozycozy allows you to easily compare brownstones, lofts, and apartments across different neighborhoods, ensuring you secure the perfect base camp for your journey.
To narrow your search down, we recommend looking at these incredible neighborhoods for a taste of the Chicago good life.
Wicker Park
Wicker Park is full of creative expression. The architecture is everything you imagine the old Chicago to be, with a true gritty, eclectic urban vibe that defined the 60s/70s/80s in Chicago.
There are so many cool vintage shops and record stores that you might need to bring an extra suitcase with you so that you have room to bring things home. And the underground music venues are insane if you fancy some drinks and live music.
The coffee house culture is also really cool here.
If you catch the CTA Blue Line, you’re only 8 to 15 minutes away from downtown stations like Clark/Lake or Jackson.
And, interestingly, it’s 17% safer than other US neighborhoods.
Lincoln Park
The views from the Lincoln Park area are amazing. The park runs alongside the picturesque Lake Michigan, so you have little areas of beach access and plenty of park space to sit with a picnic and watch the world go by. Two of the most popular swimming spots, if you’re going in summer or when the weather is warmer, are North Avenue Beach and Diversey Beach.
We’d also recommend the Lincoln Park area for families. You’ve got the Lincoln Park Zoo and the Lincoln Park Conservatory, which are both well worth visiting. It is a little further from downtown Chicago, but if you catch the Red Line, it’ll only take 26 minutes.
The tree-lined streets and historic architecture, along with the tranquil Lake Michigan views and parks, make this neighborhood a vacation rental hotspot.
Logan Square
Logan Square is so laid-back. It couldn’t be more opposite to the hustle and bustle of downtown Chicago. The restaurant scene is absolutely incredible (Longman & Eagle and Lula Cafe are a must).
Like a lot of Chicago that isn’t the downtown area, the historic architecture is so nice here. You really get a feel for the true Chicago, not the high-rise centre. And the wide, tree-lined boulevards anchored by the iconic Illinois Centennial Monument are so nice for strolling down after a morning coffee before you go to the Downtown area.
From Logan Square, you’ll need to take the CTA Blue Line, and you’ll be in the Downtown area in around 20/25 minutes.
Things to Do and Best Restaurant Recommendations in Chicago
Chicago is a massive state home to around 2.7 million residents, but all of the best things to do in Chicago are pretty concentrated in the Downtown area and the neighborhoods surrounding it, like the ones we’ve listed.
In our opinion, here are the best things to do:
Adler Planetarium
Chicago 360 (go to the skydeck)
Hop-on-hop-off bus city tour to make the most of a sightseeing day.
Art Institute of Chicago
Maggie Daley Park
Walk Under The Bean (Google it).
And there’s so much more we could list. Google ‘best things to do in Chicago’ and create your perfect itinerary.
As for the best restaurants, we’ll list them based on the neighborhoods we’ve recommended:
Logan Square:
Lula Cafe and Daisies.
Lincoln Park:
Pat’s Pizza and Ristorante and The Wieners Circle.
Wicker Park:
The Delta and Bongo Room
The Windy City might just blow your budget into oblivion as you devour through the mouthwatering dining scene and spend way too much on souvenirs, but at least you’ll leave with a full heart. Follow our advice on where to stay for the true Chicago experience.
