Holiday rentals in Chicago

Andersonville Luxe Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance

Gorgeous, classic Chicago brownstone with a private entrance and private bath. It is your own private apartment with a private kitchenette, private en suite bath and a private entrance. In the heart of a great city with every amenity and over 500 five star reviews! Walk to Wrigley or ride one of our free bikes. This suite is located 5 minutes from the "el" and many restaurants, boutiques and taverns. TOP 1% of all Airbnbs in Chicago after a DECADE of helping our guests in every way we can.

EZ Entry, Queen Memory Foam Bed Room, Smart TV

Sleep on a LUXURIOUS FULL SIZE MEMORY FOAM BED! Private room, free cakes & coffee, microwave and fridge is located right outside the room! Beautiful, safe area. Friendly people. 35 to 45 minutes to Chicago. Beautiful nature centers, jogging paths, lakes and parks all near by! Asian and American buffets, Olive Garden, and much more within minutes! Beautiful, safe area built around huge trees that are decades old! Water Park, bating range and more!

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Chicago Addison St. 1 bed/1 bath condo, Garden Lvl

You'll have a great time at this comfortable place, 12 minutes from o’Hare airport and 20 minutes from downtown, dunning pour house is a nice bar&restaurant just 2 buildings down from the place, which is nice you don’t have to drive or look for parking, there is a park across the street also walking distance and couple of grocery and liquor stores plus a dry cleaner also walking distance!

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

Chicago River Room near USMLE

R+ My other listings can be found through my profile page. 7 minutes to O'Hare Airport See below for details. Highway entrance 1 block away, so you can easily drive anywhere. Walking distance to pharmacy, shopping mall (including grocery store), health club, train station, restaurants and a library. 0.6 miles to Harlem Blue Line. Prices are subject to change.