Chicago Vacation Homes

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Our top choices for Chicago holiday homes

Modern 3BR Apartment Near North Ave Shops

Near North Side

HK$9,050 total

includes taxes & fees

12 Jun - 13 Jun

Master qtr close to nature & easy urban facilities

Riverwoods

Nayeli A.

HK$1,611 total

includes taxes & fees

18 Jun - 19 Jun

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

South Evanston

Shashi Y.

HK$2,625 total

includes taxes & fees

2 Jun - 3 Jun

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton

Nancy F.

HK$2,533 total

includes taxes & fees

2 Jun - 3 Jun

Near Lake and Museum • Modern • Game Area

South Shore

HK$4,995 total

includes taxes & fees

16 Jun - 17 Jun

South Loop · 3 Kings · Steps from McCormick Place

Near South Side

"This apartment had all the amenities we needed for our 3 day stay in Chicago. It was much larger than I expected and high ceilings made it feel like we were in a loft. I’m happy we made the decision to stay here rather than at a hotel, where I would’ve had to listen to people talking in the hallway or doors being slammed all night. Here, it was quiet and the location was perfect. We were just about 12 minutes from downtown, which made it convenient to drive downtown when we needed to. "

Markeisha W.

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood

Eduardo

HK$2,367 total

includes taxes & fees

1 Jun - 2 Jun

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Westmont

Tomas R.

HK$1,719 total

includes taxes & fees

26 May - 27 May

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Top Chicago Hotel Reviews

Hotel Riu Plaza Chicago

10/10 Excellent

"Solo traveler. Spacious king room. Double sink bathroom. The breakfast buffett was one of the best I've had. Convenient location to Michigan Ave and Riverwalk."

The Chicago Hotel Collection Ambassador Gold Coast

4/10 Poor

"Walking into the hotel, it's very nice. The bar stea is also very impressive. The staff were friendly and helpful. The room was a massive disappointment. Like a cross between ikea and a motel 6. It was clean but very spartan. White walls, no pictures. I expected much much more for the price. Definitely would not recommend"

Aloft by Marriott Chicago Mag Mile

4/10 Poor

"The hotel and the price are not aligned. The room is underwhelming and feels like solitary confinement. The shower didn’t drain properly so water collected and your feet were in a full tub of water. The time it took for the water to drain was several hours!!!! There is no closet to hang your clothes so prepare to have to iron. There isn’t any storage in the restroom or shelves for settling in with your personal items. The overall cost wasn’t a value, but instead we paid more than what we received. I am shocked it is a Marriott property and won’t make plans to stay with Aloft again."

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