Best Places To Stay in Chicago For Vacation Trip


Chicago, one of the most populous cities in the State of Illinois, is nestled along the shoreline of the Great Lakes. The city itself is well-known for its vibrant music scene, city life, shopping centers, futuristic architecture, gorgeous beaches, and cultural attractions.

Another fun fact about it is that although is well-known to be the “Windy City.” The truth is, it’s not even on the list of the top windy cities in the US.

Now, let’s explore one of the best places to stay in Chicago to help you decide when to stay on your next vacation trip:

Logan Square

Logan Square is made up of beautiful boulevards and a wide variety of restaurants and bars in the area.

It’s also one of the cities trendiest neighborhoods, which balances an excellent nightlife with lots of family-friendly activities in the area.

It provides a breath of fresh air especially for returning visitors who have mostly seen the major tourist destinations in the downtown area.

Drop by at the Logan Square Farmers Market, which draws in several visitors from Michigan, Wisconsin, and Southern Illinois. Aside from the fresh produce, you can also buy flowers, empanadas, tacos, hot sauce, handmade sauce, and more.


Pilsen is known to be one of the city’s most recognizable neighborhoods. With its vibrant murals and public art, you’ll get a glimpse of Chicago’s Southwest’s artistic side.

It’s also an excellent location for culture buffs as it houses the best museums the city has to offer, with stunning contemporary art galleries and a vibrant bar and restaurant scene.

The best thing about it is that it’s easily accessible via bus, Metra, or Pink Line. This fascinating southwest side of Chicago is where you can soak in both culture and entertainment.

While you’re in Pilsen, make sure to head off to The National Museum of Mexican Art, one of the most underrated attractions in the city, which features a 10,000-piece collection. It also hosts a variety of family-friendly workshops and unique rotating exhibits. The best part? The admission is free.

Craving for some mouthwatering food? Make sure to secure a reservation at HaiSous, a Vietnamese restaurant that offers best-sellers like tender mussels cooked in coconut broth and fish sauce-glazed chicken wings. You can explore the neighborhood’s endless supply of taco joints.

West Loop

If you consider yourself a foodie, then the best place to stay whenever you’re in Chicago is the West Loop. The area is known to house a variety of excellent restaurants and bars and even Michelin-star establishments like the Blackbird.

Moreover, you can easily explore a couple of attractions in downtown Chicago, because the Loop is just one train ride away.

Don’t forget to drop by the Randolph Street Market where hundreds of vendors sell various antique furniture, houseware, art, clothing, and a whole lot more in this indoor-outdoor bazaar.

You can spend your afternoon browsing through the racks of vintage finds you can use to decorate your apartment in this unique and quirky shopping destination. If you want your family to witness more exceptional beaches, see ancient ruins, and experience a unique culture, the best place to visit after Chicago is Mexico. Check out the best all-inclusive resorts in Mexico for families first before you book your tickets.


Andersonville might be a bit small, but it’s filled with unique buys from vintage boutique shops, lively bars, and live gig venues. Make the most out of the nightlife if you’re staying here. You can catch a theater or comedy show, or visit a couple of art galleries and museums.

If you’re looking forward to having a budget-friendly dinner while having an ice-cold beer, then check out Hopleaf, another neighborhood favorite.

For dessert, drop by at the First Slice Pie Cafe a lovely cafe and pie shop in the area where you can indulge your sweet tooth in best sellers like key lime, and Michigan cherry.

If you want to bring home a couple of souvenirs for year trip, there’s the Andersonville Galleria where you can easily browse through apparel, paper goods, candles, furniture, and prints. There are also a couple of shops that are locally-owned in the surrounding area.

Wicker Park and Bucktown

Wicker Park and Bucktown are vibrant hubs for both entertainment and culture in Chicago, filled with cocktail bars, restaurants, condominiums, concert venues, and shops. It’s quite easy to go there from Chicago O’Hare Airport, with a lot of transportation options like the train and bus to help you navigate.

Dove’s Luncheonette is a perfect place to eat brunch is the lovely and Instagrammable which features Southern-inspired Mexican dishes.

If you want to experience the neighborhood’s vibrant nightlife, head off to Violet Hour, a cocktail den known for its house rules- no baseball hats, no using of cellphones, no light beer. Soak in Chicago’s famous craft scene as you get to try out a menu of stirred and shaken concoctions.

If you have some free time to kill, why not hop on to 606, a walkway that stretches through several surrounding neighborhoods. On the trail, you’d come across several parks, shops, and cafes to fill your afternoons.

Gold Coast

Gold Coast is the city’s historic district and became a popular neighborhood back then during the wake of the Great Chicago Fire.

It was back in 1882 when millionaire Potter Palmer moved here, building a 42-room castle-like building. Other people followed, and today, it’s known to be one of the most high-end neighborhoods in the city.

Here, you can find spectacular skyscrapers, stunning mansions, specialty boutiques, and several Michelin-starred establishments. Oak Street is known to be the shopping district in the area, while Rush Street is where the best nightlife is found. The place is ideal if you’re a traveler seeking for luxury.

Final Thoughts

Figuring out the perfect place to stay in Chicago can be a tough decision. Most travel websites will probably recommend you in staying in the downtown area. But the thing is, it’s already filled with big hotels and lots of tourist traps.  Deciding to possibly move then be sure to check out options like Gold Coast removalists as a great option.

If you want to explore Chicago like a local, and contemplating for a place to stay, then consider these cool neighborhoods and these top Airbnb Chicago Rentals. All are easily accessible in the downtown area, and you can easily use public transportation.


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