Photo by throwingsofas
Northwest Side Vacation Rentals
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Northwest Side Vacation Homes

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
6.6 out of 10, (4)
The price is CA $205
CA $326 total
includes taxes & fees
Aug 13 - Aug 14

Great 3 bedroom rental unit near Logan Square
Great 3 bedroom rental unit near Logan Square
9.6 out of 10, Exceptional, (51)

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
8.0 out of 10, Very good, (3)
The price is CA $310
CA $626 total
includes taxes & fees
Sep 9 - Sep 10

Vintage Urban Retreat
Vintage Urban Retreat
10.0 out of 10, Exceptional, (9)
The price is CA $229
CA $695 total
includes taxes & fees
Aug 20 - Aug 21

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
2.0 out of 10, (1)
The price is CA $217
CA $1,248 total
includes taxes & fees
Aug 13 - Aug 14

Walk to the Beach! Theater-Coffee Bar-Games-Gym
Walk to the Beach! Theater-Coffee Bar-Games-Gym
9.6 out of 10, Exceptional, (10)

LakeHouse
LakeHouse
9.2 out of 10, Wonderful, (20)

Cozy 3-bedroom house in family-oriented Melrose Park.
Cozy 3-bedroom house in family-oriented Melrose Park.
10.0 out of 10, Exceptional, (20)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Top Northwest Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG
10/10 Excellent
Find out more about Northwest Side
Find out more about Northwest Side
Northwest Side Vacation Homes information
Number of reviews | 433 |
---|---|
Accommodation | 431 Vacation Homes |
Lowest Price | CA $137 |
Highest Price | CA $310 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Vacation Homes in Other Destinations
More Accommodation Types in Northwest Side
- Apartments in Northwest Side
- Condo Rentals in Northwest Side
- Motels in Northwest Side
- Aparthotels in Northwest Side
- B&B in Northwest Side
- Cottages in Northwest Side
- Guest Houses in Northwest Side
- Hostels in Northwest Side
- Resorts in Northwest Side
- Villas in Northwest Side
- Farmstay in Northwest Side
- Hotels
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2025
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes
More ways to book
Expedia's Latest Trends
Hotels
- Canada Place Cruise Ship Terminal hotels
- Soldier Field hotels
- United Center hotels
- McCormick Place hotels
- Wrigley Field hotels
- Sandos Playacar All Inclusive
- Lollapalooza hotels
- Motels Brampton
- Delta Hotels by Marriott Vancouver Downtown Suites
- Mere Hotel
- Michigan Avenue hotels
- Art Institute of Chicago hotels
- Hotels in Clearwater
- Millennium Park hotels
- Chicago Riverwalk hotels
Flights
Activities