The Best Airbnbs for Groups in Chicago – the Best Houses to Rent fo Bachelor and Bachelorette Parties

Heading to Chicago with a group this summer? With all that the Windy City has to offer, why settle for a hotel when you have incredible airbnbs like these to choose from! A unique airbnb can really set the tone for the type of party you’re looking to create and make it a more inclusive environment! A spacious Airbnb allows for people to gather in the kitchen around charcuterie or relax and chat in the living room in-between festivities. From updated lofts, historic homes and newly built penthouses – I’ve scoured the internet to bring you the best Airbnb’s for groups in Chicago!

Vibey Refurbished Loft in Old Town

5 Bedrooms, 8 Beds, Sleeps 16

Price: $697/night ($49/person per night with 14)

Located in the heart of downtown, you’ll be within walking distance of all the happening spots and there is a parking garage right across the street. This beautiful 4,000 sqft home is actually two combined units connected via a spiral staircase, so you’ll actually have two kitchens!! The modern exposed brick and high ceilings blended with the antic eclectic furniture gives the space a luxurious artist loft vibe!

Luxe New Construction in Logan Square

4 Bedrooms, 6 beds, Sleeps 12-16

Price: $913 ($65/person per night with 14)

Logan Square is a trendy thriving neighborhood filled with amazing art, restaurants and great architecture. This is a great option if the bride is a foodie because it is located just off of Armitage Avenue in what is known as the “second restaurant row” of Chicago. You are a short walk away from Scofflaw, Giant, Parson’s, Moonlighter and many more of the best restaurants and bars in the city!! This home also has an adorable outdoor patio, perfect for summer pregames!

Mid-Century Modern in Lakeview

3 Bedrooms, 5 Beds, Sleeps 10-12

Price: $850/night ($85/person per night with 10)

Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. There is plenty of shared space and even a little garden patio for outdoor dinners in the summer months, too!

Colorful Condo in Wicker Park

5 Bedrooms, 9 beds, Sleeps 16

Price: $912/night ($65/person per night with 14)

Flamingos, marlins, and sharks along with tropical florals and bright colors makes for a chic beachy themed space in Chicago. I don’t know about you guys, but I loved themed rentals! It makes it feel like you’re at a boutique hotel rather than someone’s home. This spot in particular has raving reviews and is located 1 block away from the Blue line which will take you directly into town or to the airport! Easy enough! I’m ready for taco night and margaritas!

Bohemian Luxury in Lincoln Park

6 bedrooms, 7 beds, Sleeps 14

Price: $2,450 ($175/person per night with 14)

A whimsical, modern and cozy home in the heart of residential Lincoln Park with lots of lounging areas. This is a truly unique home with TONS of outdoor living space to enjoy, complete with sauna and ping pong table. Walkable to Wells and Armitage shopping districts and North Ave beach, you’ll be steps away from plenty of restaurants and coffee shops!


Designer Loft in Fulton Market

5 Bedrooms, 14 beds, Sleeps up to 24

Price: $596/night ($42/person per night with 14)

This gorgeous open concept loft is on the 2nd floor of a historic 1920’s building overlooking Fulton Market. Once inside, you’re greeted by a 5,000sft living space with soaring windows, polished concrete floors, and exposed brick details. The upscale furnishings and designer touches are sure to create an unforgettable stay!

Brand New Units in River North

10 Bedrooms, 20 beds, Sleeps 20

Price: $1,856/night ($132/person per night with 14)

You’ll have the entire building, which include 4 brand new modern units with rooftop patios! Located in the booming River North district, you’ll be just a short walk to Michigan Ave, Magnificent Mile, Navy Pier, and endless amazing bars and restaurants!! With a total of 20 beds, this is the perfect spot if you plan on having a large group for your bachelorette party!

Tropical Penthouse Wicker Park

4 Bedrooms, 5 Beds, Sleeps 10

Price: $693/night ($69/person per night with 10)

Tropical tiki vibes, but make it modern. This funky fresh home is nestled right in the middle of Wicker park, a trendy neighborhood close to downtown. Ask about a private chef, photo booth and karaoke!! Such a fun spot for a memorable bachelorette weekend. 

Swanky Loft in River West

4 Bedrooms, 7 Beds, Sleeps 14

Price: $1,950 ($139/person per night with 14)

This 3 level and 4,000 sqft luxury loft sits in the River West district, essentially a 5 minute uber ride from wherever you want to go! Think marble bathrooms, plush bathrobes, open concept kitchen and rock n roll vibes! This is a great spot for a bride who appreciates the finer things in, like a well stocked bar. 


The Orleans Building in River North

8 Bedrooms, 16 beds, Sleeps 16+

Price: $1,113/night ($79/person per night with 14)

An entire building comprised of 4 suits, this luxury townhome is located in the River North District. You’ll be right downtown next to all the best bars and restaurants, plus you have a roof-top deck with incredible views! Perfect for sunset drinks! Great for large groups, with 16 beds!!

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Christina is a leading luxury lifestyle and travel blogger with over 2 million readers. Follow her on instagram @jetsetchristina.