Vacation rentals in Chicago

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Top-rated vacation rentals in Chicago

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Top guest favourite

Private room in Elmhurst

4.99 out of 5 average rating, 217 reviews

Chic Oasis near Downtown Chicago

Open the classic wooden shutters and let in the morning sun at this peaceful abode in the suburbs. The kitchen fridge and small appliances, family room, upstairs laundry, and basement game tables. We enjoy hosting our guests and are happy to help with any information and/or suggestions to make their visit as enjoyable as possible. Located in a quiet suburb, there's a park with tennis courts and a playground within walking distance. A short Uber or taxi ride reaches dozens of excellent restaurants and shops in locations such as the cozy downtown Elmhurst area. We are 10 minutes away from public transportation from Elmhurst to downtown Chicago. If you have a vehicle, parking is inexpensive at the Elmhurst train station. If you do not have a vehicle, we recommend taking Uber or Lyft to the Elmhurst train station. If you are planning to drive into the city of Chicago, we recommend using either SpotHero or ParkWhiz parking apps. We will try to make your stay as comfortable as possible. If you have any special needs or requests, please let us know and we will do our best to accommodate you.

Top guest favourite

Apartment in West Ridge

5 out of 5 average rating, 31 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Guest favourite

Apartment in Oak Park

4.91 out of 5 average rating, 67 reviews

Studio Mins Walk to DT OAK PARK

You will find yourself having a comfortable stay at this centrally located studio just a 5 minute walk from Frank Lloyd Wright Home & Studio, surrounded by beautiful homes yet right next to a variety of shops, cafes and restaurants with Petersen's Ice Cream being right next door, Broken Tart cafe, and Giordano's Pizza right across the street, enjoy the beautiful architecture on a scenic 10 minute walk from this studio to Downtown Oak Park for an even bigger selection of dining and entertainment.

Superhost

Private room in Oak Park

4.73 out of 5 average rating, 298 reviews

Little Gem Double Rm Home Base for Chicago Trips!

Great home base for Chicago adventures & PREMIUM location in the epicenter of Oak Park - America's home of prairie architecture! Beautiful park/Frank Lloyd Wright homes are directly outside your door and you are only a 25-minute train ride to Millennium Park & all of Chicago! Eclectic garden level (shared) apartment decorated with fun and funky furnishings. Private Bedroom with new double size bed, deluxe bedding, towels. Shared bathroom, living room, and kitchenette. View my other 2 listings!

Guest favourite

Private room in West Rogers Park

4.95 out of 5 average rating, 193 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.

Guest favourite

Private room in North Riverside

4.93 out of 5 average rating, 215 reviews

The Albany Park Room at the Cape Cod in Riverside

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 Riverside's historic downtown and Loyola University Medical Center. O'Hare Airport is 18 miles away, and Midway is 9 miles. The Albany Park Room, one of two Airbnb listings, is on the second floor and accommodates two guests. The property supports sustainability with partial solar energy for heat and hot water.

Guest favourite

Apartment in Portage Park

5 out of 5 average rating, 5 reviews

LairBnB - Garden Apartment

Welcome to LairBnB! This is a private garden apartment with separate egress in our home near 6 corners in Portage Park. The ceiling height is 76”. Guests under 6' tall will be most comfortable here. We are old school Airbnb SuperHosts who love to host adult travelers in town for work or events in Chicago. We are steps away from Milwaukee, Cicero, and Irving Park bus stops, an 8 minute walk to the Grayland Metra stop, and a 20 minute walk to the Irving Park Blue line CTA.

Superhost

Apartment in Near South Side

4.69 out of 5 average rating, 87 reviews

McCormick Place Studio/parking/sleeps up to 4

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Sofa bed for 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

Guest favourite

Private room in Chicago

4.84 out of 5 average rating, 528 reviews

Egyptian Room - Free Parking, 1 block to CTA

Comfortable lower level bedroom with a pillow top king bed, granite topped desk, and smart tv makes this room a super cozy retreat, You will have full access to the kitchen cooking and free Keurig coffee. You have a private mini fridge in your room for food storage. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms. Easy unmetered street parking is readily available for those coming by car.

Superhost

Apartment in Berwyn

5 out of 5 average rating, 5 reviews

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

Guest favourite

Private room in Hyde Park

4.92 out of 5 average rating, 273 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

Apartment in Pilsen Historic District

4.94 out of 5 average rating, 54 reviews

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.