Vacation rentals in West Side

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Top-rated vacation rentals in West Side

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

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Guest favorite
Private room in Melrose Park
4.95 out of 5 average rating, 102 reviews

4 miles to Airport, King bed. Near expressways.

Room near O'Hare airport (4 miles), 7 min walk to the bus or 6 minute car ride to the Metra train to Chicago. 13 min to Allstate Arena, 11 min to Donald E. Stephens Convention Center or Rosemont Theatre . 10 min to Fashion Outlets mall or Entertainment District (bars and restaurants and concerts and comedy club/ casino. Room:1-2 adults, Near expressways 294 / 88 / 90 Towels provided Luggage drop off prior to check in Please send me a picture if profile does not have one prior to arriving.

Guest favorite
Apartment in Oak Park
4.84 out of 5 average rating, 232 reviews

Betty BnB

Free admission to The World's Smallest Betty White Museum! Oh, and a comfortable king-sized bed in a newly updated studio apartment. Centrally located in Oak Park, close to cafes and transit. Quiet, friendly neighborhood with ample street parking and a pub across the street. This is a basement unit with a kitchenette (NO STOVE/OVEN), cozy TV room, desk nook, and full bathroom. The bed is king-sized and has a firm mattress. The floors slope and there's no thermostat, but it's cute + welcoming

Guest favorite
A cozy corner of the shared space is displayed, featuring a blue velvet loveseat adorned with two golden pillows. A small wooden table sits in front, accompanied by a bright yellow ottoman. A decorative wall art piece and natural light from a window enhance the inviting environment.
Private room in Chicago
4.76 out of 5 average rating, 159 reviews

G1. Next to Downtown! Best location

Bedroom for rent in the desirable neighborhood of Lakeview. Location is its most important fact. It is right in front of one of the biggest supermarkets(Whole Foods). There are multiple stores just one block away such as target, xsport fitness, banks. Different restaurants and more. Walkable to brown line train to go downtown as well as bus stops to go all possible directions. Beautiful apartment, bedroom with closet. All you can think of at a great price. host lives in the same apt

Top guest favorite
Private room in Chicago
4.99 out of 5 average rating, 349 reviews

Private Bed and Bathroom in a Great Location

Located in Ukranian Village, the new "hot" neighborhood, it's close to many great eateries and pubs. A beautiful yard filled with flowers and plants and a large deck in back with a canopy to sit outside and unwind at the end of the day. Inside is very comfy. A combination of vintage and modern. The guest room has a queen size mattress and curtains heavy enough to block out the street lights. Its one short block from Chicago Avenue and the #66 bus that goes down town.

Guest favorite
Private room in Chicago
4.78 out of 5 average rating, 540 reviews

Garden Room - King Bed, Sofa Bed, 1 Block to Train

This room is in the lower level of Fort Washington, a Richardsonian Romanesque mansion. Brick/Limestone walls create a cozy room a perfect retreat after a long day in Chicago. 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. There is non metered street parking out front.

Top guest favorite
The living room features two large windows allowing natural light to fill the space. A red sofa and black armchair provide seating, with a small white table beside the couch. A green plant adds a touch of nature, and a piano stands elegantly to the side.
Private room in Chicago
4.95 out of 5 average rating, 396 reviews

A+ location by Mag Mile, views, large sunny room

Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. Apartment is shared with single host (covid-vaccinated), happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/respectful host, Flexible luggage policy, fast wifi)

Guest favorite
A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.
Apartment in Chicago
4.95 out of 5 average rating, 147 reviews

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Superhost
Private room in Chicago
4.77 out of 5 average rating, 337 reviews

Chicago River Room near Resurrection Med Ctr

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 favorite
A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.
Condo in Chicago
4.97 out of 5 average rating, 851 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.

Guest favorite
Private room in Chicago
4.83 out of 5 average rating, 563 reviews

The Blue Room

A spacious single-family home; minutes away from Midway Airport (train station), within walking distance from gorgeous and dog-friendly parks, and walking distance of plentiful of supermarkets and convenience stores. Downtown Chicago is just about 40 minutes away from a train ride.

Top guest favorite
A vintage living room is displayed, featuring a mix of upholstered chairs and a wooden table. A mahogany cabinet showcases decor items, while a piano can be seen in the background. A patterned rug covers the floor, enhancing the room's cozy and historical ambiance.
Private room in Oak Park
4.95 out of 5 average rating, 406 reviews

Antique Filled Home

Our warm and inviting home is located in historic Oak Park, home of Frank Lloyd Wright and Ernest Hemingway. The green line will whisk you to the center of Chicago in 25 minutes and it is less than three blocks from our front door.

Guest favorite
Private room in Chicago
4.83 out of 5 average rating, 232 reviews

BOHEMIAN LODGE #4 ( clean & affordable travel)

Pilsen neighborhood = best in Chicago!! PRIVATE SPACE - BEDROOM & ATTACHED PRIVATE BATHROOM CLICK "show more " below BEFORE YOU BOOK/INQUIRE Please read and respond to our house rules. No smoking No visitors

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