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Holiday Homes in Northwest Side

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Featured Holiday Homes in Northwest Side and around

Our top choices for Northwest Side holiday homes

2 Connecting Suites at a 4⭐️ Hotel

The price is €649
includes taxes & fees
2 Sept - 3 Sept
2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 5⭐️ Hotel

The price is €3,142
includes taxes & fees
1 Sept - 2 Sept
2 Connecting Suites at a 5⭐️ Hotel

Chic Studio in Heart of Chicago

The price is €175
includes taxes & fees
24 Aug - 25 Aug
Chic Studio in Heart of Chicago

Comfy Studio in Portage Park- Great Value!

The price is €168
includes taxes & fees
24 Aug - 25 Aug
Comfy Studio in Portage Park- Great Value!

4BR Retreat w/ Theater, Game Room & Backyard

8.8 out of 10, Excellent, (6)
The price is €434
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard

2BR Traveler's Favorite, Modern and Clean

10.0 out of 10, Exceptional, (1)
"The place was really nice and clean, an excellent stay that ill consider again my next trip to chicago"
The price is €317
includes taxes & fees
26 Aug - 27 Aug
2BR Traveler's Favorite, Modern and Clean

Prime City Stay in a 1BR Apt

9.0 out of 10, Wonderful, (6)
The price is €170
includes taxes & fees
16 Sept - 17 Sept
Prime City Stay in a 1BR Apt

Cozy 2BR Apt for a Seamless Stay

8.0 out of 10, Very good, (1)
"Everything as advertised. The only part that I was unsure of was what to do with the keys as this was not stated in any of the information provided. So I left them on the table. "
Cozy 2BR Apt for a Seamless Stay

Cozy 2BR Apt w/ Washer & Dryer

Cozy 2BR Apt w/ Washer & Dryer

Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

9.0 out of 10, Wonderful, (2)
"It was nice and everyone was very friendly!!"
The price is €126
includes taxes & fees
31 Aug - 1 Sept
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

1BR Gem by Shops & Dining

1BR Gem by Shops & Dining

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is €798
includes taxes & fees
23 Sept - 24 Sept
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

1BR Vibrant & Inviting Apt in Chicago

4.0 out of 10, (1)
"My impression of the property at 1st was cute.... AT 1ST! Until you see dog mess from tenants not curbing their dog. The apt is on the 2nd floor & can't use AC and other appliances unless you want a breaker blowout & waiting hours for reset. Choose another place."
1BR Vibrant & Inviting Apt in Chicago

2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

The price is €468
includes taxes & fees
5 Sept - 6 Sept
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

2BR w/ Workspace + Coffee Bar • Near Transit

6.0 out of 10, (2)
"Newly refurbished apartment space was lovely! Management company was easily accessible and was very helpful. The heat of the summer kept the space a little warm (has two AC window units). "
The price is €381
includes taxes & fees
31 Aug - 1 Sept
2BR w/ Workspace + Coffee Bar • Near Transit

Cozy Studio in Portage Park

Cozy Studio in Portage Park

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is €354
includes taxes & fees
24 Aug - 25 Aug
Cozy house in the city

Cozy Room with Rooftop Lounge & City Views in River North

10.0 out of 10, Exceptional, (1)
"The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good."
The price is €237
includes taxes & fees
1 Sept - 2 Sept
Cozy Room with Rooftop Lounge & City Views in River North

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is €193
includes taxes & fees
2 Sept - 3 Sept
The One: A 1BR Stay That Feels Like Home

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (4)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
The price is €194
includes taxes & fees
2 Sept - 3 Sept
Stylish 1BR in West Loop
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.
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Top Northwest Side Hotel Reviews