Apartment
9.0(1 Review)
3 Bedrooms
8 Guests
Parking
Kitchen
Air Conditioner
Internet
US $196/Night
West Side stays by Sonder
West Side cities run on errands, dinners, and late returns.
Sonder West Side Places to Stay
West Side, Illinois works for Chicago trips, from neighborhood dinners and museum days to quick city weekends. Start with the part of the metro that fits your plans, then find Sonder apartment-style stays and boutique hotels close to where you are headed.
Regions of West Side
Corners of West Side worth settling into.
Every region keeps its own pace. Browse the areas of West Side where Sonder has stays, then narrow down to the city you want to wake up in.
West Side city stays
Downtown streets, city lights, and neighborhood mornings.
From Chicago's street life to Springfield's government district and Peoria's riverfront pace, choose the city that places you closest to the Illinois itinerary you have in mind.
West Side by stay type
Find the right kind of stay.
From boutique hotels in the middle of everything to apartment-style stays built for settling in, browse West Side by the kind of place that fits your trip.
West Side stays
9.0
9.7
9.5
8.5
9.2
9.0
10.0
9.4
8.2
8.9
9.3
8.9
8.9
8.8
8.9
8.0
Curated stays across West Side cities you came for.
A curated edit of apartment-style stays and boutique hotels across West Side, so you can see the range before you narrow down.
9.0
Apartment
9.7(4 Reviews)
3 Bedrooms
7 Guests
Hot Tub- Parking
- Air Conditioner
- Internet
US $714/Night
Apartment
9.5(98 Reviews)
3 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
Child Friendly
US $172/Night
Apartment
8.5(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $320/Night
Apartment
9.2(5 Reviews)
3 Bedrooms
10 Guests
- Parking
Balcony/Terrace- Internet
- Child Friendly
US $438/Night
Hotel
9.0(217 Reviews)
Breakfast- Parking
Pool- Balcony/Terrace
US $381/Night
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
View- Kitchen
US $345/Night
Hotel
9.4(29 Reviews)
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $284/Night
Apartment
8.2(19 Reviews)
2 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
Sports/Activities
US $260/Night
US $427/Night
Apartment
8.9(18 Reviews)
6 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Accessibility
US $513/Night
Apartment
9.3(6 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
Wheelchair Accessible
US $354/Night
Aparthotels in West Side
Over 6+ Apartment-Style Stays with Hotel Comfort in West Side
Hotel
8.9(497 Reviews)
Private Pool- Breakfast
- Parking
- Pool
US $215/Night
Hotel
8.9(182 Reviews)
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $185/Night
Hotel
8.8(430 Reviews)
- Breakfast
EV Charge Station- Parking
- Balcony/Terrace
US $229/Night
US $258/Night
Hotel
8.9(904 Reviews)
- Parking
- Kitchen
- Air Conditioner
- Internet
US $203/Night
Hotel
8.0(643 Reviews)
Private Beach
Oceanfront- Breakfast
- EV Charge Station
US $299/Night
Good to know
West Side travel questions, answered.
Quick answers to the questions travelers ask most.
01 / 07
What are the top Boutique Hotels and Aparthotels in West Side?
Discover top family-friendly travel options in or near West Side. If you're planning a trip or vacation to West Side, consider spending a week or two at any of our welcoming family-allowed hotels, resorts, or other recommended properties. These are renowned as the Top Vacation Rentals and Places to Stay in West Side:
- Modern 4BR Pilsen Retreat Near Illinois Medical District & Chicago Downtown
- West Loop - City Views With In & Out Parking 4
- Stylish 5BR West Loop Retreat with Optional Parking
- LIVN West Loop Chicago 1 BR
- Little Italy 5BR Stay with Optional Parking
- Little Italy 4BR Retreat with Optional Parking
- Stylish brand new 3BR Near West Loop and Fulton Market
- Luxury 2BD-2BA View-Gym-Rooftop
- 15 mins DT HumboldtPark Gem Sleeps 8 FreePark
- First floor Condo in Chicago
02 / 07
How many Boutique Hotels, Aparthotels, and Urban Apartments are available in West Side?
Sonder™ regularly updates its listings to offer a diverse selection of accommodations, each with clear details on family amenities. Currently, there are over 53 active properties listed by Sonder in 2026 in the West Side area, with new additions daily. By aggregating listings from various websites and travel providers, Sonder delivers a vast array of top places to stay that are perfect for families visiting West Side.
03 / 07
Which part of West Side works best if I want an easy city base?
Choose West Side if you want a practical base with direct city access and a local feel. It works well for travelers who plan to spend most of their time out in the city and want a straightforward place to return to each night. Check the listing for exact transit and building details.
04 / 07
Is West Side a good fit for a short weekend stay or a longer visit?
West Side works for both, but it is especially useful if you want a weekend centered on neighborhood exploring and simple transit connections. For longer stays, look for apartment-style layouts and workspace amenities where available. The listing will show whether a stay is set up for multiple nights.
05 / 07
What is the easiest way to get around from West Side?
Plan to use transit, rideshare, and walking, with exact options depending on the building. West Side is a good fit if you want to move between neighborhoods without relying on a car for every trip. Check the listing for parking, nearby transit, and building-specific access details.
06 / 07
When is the best time to book a stay in West Side?
Book West Side when you want a city stay with steadier foot traffic and easier access to neighborhood routines. Spring through fall usually suits travelers who want to spend more time outdoors and moving around the city, though your ideal timing depends on your plans and tolerance for weather shifts.
07 / 07
Is West Side a good choice for food, remote work, or a quieter stay?
West Side can work well for food-focused trips, remote work, or a lower-key city base, depending on the exact building and block. If you need a strong workspace setup, quiet hours, or a kitchen, verify those details on the listing before booking. Nearby walkability also varies by address.
Discover top family-friendly travel options in or near West Side. If you're planning a trip or vacation to West Side, consider spending a week or two at any of our welcoming family-allowed hotels, resorts, or other recommended properties. These are renowned as the Top Vacation Rentals and Places to Stay in West Side:
- Modern 4BR Pilsen Retreat Near Illinois Medical District & Chicago Downtown
- West Loop - City Views With In & Out Parking 4
- Stylish 5BR West Loop Retreat with Optional Parking
- LIVN West Loop Chicago 1 BR
- Little Italy 5BR Stay with Optional Parking
- Little Italy 4BR Retreat with Optional Parking
- Stylish brand new 3BR Near West Loop and Fulton Market
- Luxury 2BD-2BA View-Gym-Rooftop
- 15 mins DT HumboldtPark Gem Sleeps 8 FreePark
- First floor Condo in Chicago
Sonder™ regularly updates its listings to offer a diverse selection of accommodations, each with clear details on family amenities. Currently, there are over 53 active properties listed by Sonder in 2026 in the West Side area, with new additions daily. By aggregating listings from various websites and travel providers, Sonder delivers a vast array of top places to stay that are perfect for families visiting West Side.
Choose West Side if you want a practical base with direct city access and a local feel. It works well for travelers who plan to spend most of their time out in the city and want a straightforward place to return to each night. Check the listing for exact transit and building details.
West Side works for both, but it is especially useful if you want a weekend centered on neighborhood exploring and simple transit connections. For longer stays, look for apartment-style layouts and workspace amenities where available. The listing will show whether a stay is set up for multiple nights.
Plan to use transit, rideshare, and walking, with exact options depending on the building. West Side is a good fit if you want to move between neighborhoods without relying on a car for every trip. Check the listing for parking, nearby transit, and building-specific access details.
Book West Side when you want a city stay with steadier foot traffic and easier access to neighborhood routines. Spring through fall usually suits travelers who want to spend more time outdoors and moving around the city, though your ideal timing depends on your plans and tolerance for weather shifts.
West Side can work well for food-focused trips, remote work, or a lower-key city base, depending on the exact building and block. If you need a strong workspace setup, quiet hours, or a kitchen, verify those details on the listing before booking. Nearby walkability also varies by address.
