
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.

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.

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

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

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.

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.

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)

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!

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.

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.

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.

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.

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
Popular amenities for West Side vacation rentals
Other great vacation rentals in West Side

T4- Room - 15 min to Red Line

Comfortable Private 1 bedroom

B1 - Next to Downtown Chicago - Private Room

O33. Next to Downtown

Frida 2720 (2F)

23rd Pl 2U

R55- Tiny Bedroom in share Apt

1 Private bed room by the beach
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- The Beverly Country Club
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- Wilmot Mountain Ski Resort
- The 606
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