Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Private room in West Rogers Park

4.94 out of 5 average rating, 209 reviews

Welcoming Evanston Home

We have a newly renovated suite awaiting your stay, perfect for one guest. This dedicated entry, private room + bathroom, and tree-lined street are in our quiet neighborhood in beautiful Evanston, just north of Chicago. As international travelers ourselves, we love hosting others from near or far! Enjoy a short walk to cafes, stores, mall shopping, parks, and restaurants. Easy free parking, convenient Uber / Lift rides, and public transportation are also here to make your stay enjoyable.

Flat in The Loop

4.8 out of 5 average rating, 319 reviews

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.

Guest favourite

Private room in Bolingbrook

4.83 out of 5 average rating, 165 reviews

SUPER MEMORY FOAM BED, EZ smart entry. Cable TV

Enjoy a super sleep on a queen size SUPER LUXURY memory foam bed! Couch, desk & more. Beautiful, safe area , homes built around huge trees that are decades old! Water Park, bating range, shopping, Great BUFFETS and other restaurants near! Free Netfil &Prime, Wi-Fi, Free access to laundry room (for stays 2 or more days) Microwave, fridge, spring water & more outside room. Enjoy sitting in one of the several outdoor seating arrangements either on the balcony or on the ground floor

Superhost

Private room in North Riverside

4.91 out of 5 average rating, 312 reviews

The Sable Creek Room at the Cape Cod in Riverside

Welcome to your home away from home! The Cape Cod in Riverside is 10 miles from downtown Chicago, accessible via METRA and CTA Blue Line. It’s a block from a trail entrance, a mile from Brookfield Zoo, and close to Loyola University Medical Center. Conveniently located, it’s 18 miles from O’Hare Airport and 9 miles from Midway. The Sable Creek Room, one of two Airbnb listings, is the only bedroom on the main floor and accommodates two guests. The property partially uses solar energy.

Guest favourite

Flat in Near North Side

4.82 out of 5 average rating, 794 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Superhost

Private room in Little Italy

4.82 out of 5 average rating, 205 reviews

ChicagoRiver Double Room

Nicely decorated Private (10x11 sq ft) Room w/designated work station, well-lit, *shared common bathroom* (other guests may be in the premises). This is NOT a full condo rental; just 1 room. Quiet & clean, 2 miles from downtown, walking distance to dozens of restaurants in Taylor Street & Little Italy. Perfect location in a quiet neighborhood, but still close to the city to enjoy food& music festivals, free concerts in Grand Park, Museums, Broadway shows, etc

Guest favourite

Shared room in West Rogers Park

4.83 out of 5 average rating, 180 reviews

05a. Common Room King

We have a King-sized bed in a Common Room. This is in a shared common room space. Up to 3 other guests my be booked in this room. The room has limited storage and NO DOOR. This space is best for those with little to no bags. Breakfast is included in your stay. We keep the pantry stocked with eggs, bacon, milk, orange juice, jam, bread, fruit, pancake mix, coffee and tea. Any of these items can be used to make yourself breakfast in the morning.

Guest favourite

Private room in Hyde Park

4.92 out of 5 average rating, 280 reviews

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.

Guest favourite

Private room in Des Plaines

4.88 out of 5 average rating, 358 reviews

R1 Delightful room in quiet neighborhood

A cozy room located in peaceful neighborhood, a perfect place to stop after traveling from O'Hare airport! We have a beautiful wild river, lake, and forest right in the backyard and surrounding our area, with wild life creating a cozy atmosphere, amazing to take walks. We are a 10 minute ride from the O'Hare International Airport, a 5 minute ride from a Metra Station, and surrounded by all kinds of parks and interesting restaurants.

Flat in Streeterville

4.71 out of 5 average rating, 350 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

Guest favourite

Private room in Norwood Park

4.77 out of 5 average rating, 326 reviews

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.

Top guest favourite

Apartment in West Town

4.97 out of 5 average rating, 828 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.