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5 Amazing Places To Stay in Chicago To Mark Off Your Bucket List

Chicago is home to famous architecture and design. For those looking to check off some boxes from the bucket list, considering renting any of the homes on this list for a group trip, intimate party or luxurious weekend getaway. These epic places to stay in Chicago do not come cheap and are surely a splurge for most. If you are willing to pay top dollar for decadence and want to plan a trip, check out our favorite places to stay in Chicago.

1. Humboldt Park Hip

airbnb.com
airbnb.com

This large three-bedroom condo packs so much style into every inch of this rental. Located in the Humboldt Park neighborhood of Chicago, this home showcases beautiful art pieces throughout.  It also embraces geometric elements and features delightful pops of color. Perfect for group trips or perhaps a girls’ weekend, guests will enjoy the attention to detail in the design. The bed-mounted with rope is also very truly unique, and the rest of the apartment offers visitors modern comfort.

2. Luxury In The Loop

JHT Studios
Airbnb.com

At the highest price on this list, we decided to save this epic rental for last. This apartment has one of the best views in all of Chicago. Directly out of the main window is one of a kind view of the historic John Hancock Tower, and is drenched in luxury from the fixtures to the furniture. From the unique curved wrap-around patio are views of Navy Pier and surrounding Lake Michigan. The breathtaking views extend to the master bedroom, offering a truly amazing experience for guests.

3. Wicker Park Worship Space

Airbnb.com
Airbnb.com

This amazing apartment in popular Wicker Park, Chicago is located inside of a converted one-hundred-year-old church. The owners opted to keep the beautiful stained glass features in the main windows. The unit is bright and airy, with minimalist furnishings that allow the light and wood to be the star. The master bedroom is at the top of the loft, featuring the top of a stained glass element, also giving guests privacy from the busy neighborhood surrounding.

4. The Historic Florsheim Mansion

Airbnb.com
Airbnb.com

This ultra-modern home was designed and built by two famous architects, Andrew Rebori and Bertrand Goldberg. The lovely mansion is something straight from the movies and serves as a relaxing retreat hidden inside Chicago’s Gold Coast neighborhood. The Gold Coast is the home to the city’s upscale shopping district, not too far from the Magnificent Mile. The dreamy, art-covered walls of this unit are complemented by the unique glass features. Guests can live like a famous artist for their stay.

5. Logan Square Luster

airbnb.com
airbnb.com

This masculine, loft-style unit takes its inspiration from the desert, utilizing animal busts, desert plants, feathers, and bright colors. The artistic style of the decor also fits perfectly into Chicago’s Logan Square neighborhood. There are four bedrooms and plenty of room for you and your guests. The minimalist decor is also made warmer by the details in the accent pieces. The textile colors and textures bring life to this desert-inspired unit. Visitors will fall in love with the exposed brick walls and animal hide floor coverings during their trip.


If you’re looking for the best places to stay in Chicago, you’ll be hard-pressed to find a better option than any of the ones listed here.