Holiday Rentals Chicago from ฿2,521: Find Short-Term Rentals & Holiday Accommodations

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Top Holiday Rentals in Chicago

Relax in a spacious area with comfortable seating and lush greenery.

"We would stay here again. Very happy with our stay "

฿7,712 total

includes taxes & fees

25 Aug - 26 Aug

Enjoy a minimalist retreat with a large bed, desk, and compact kitchenette.

"The property canceled on us 4 hours prior to check in"

฿4,829 total

includes taxes & fees

17 Aug - 18 Aug

Located in a bustling urban area, this high-rise building offers stunning city views.

"Finding a park is hard and the process of getting a room is very tedious but still very beautiful I’ve been twice "

฿11,576 total

includes taxes & fees

12 Aug - 13 Aug

Relax on the spacious balcony with a city view, featuring a sofa, armchair, and outdoor seating area.

"Nice views and convenient location to transit and dining"

Enjoy a city view from the large window, with a comfortable sofa and potted plant adding to the inviting atmosphere.

"I would stay again. "

฿5,726 total

includes taxes & fees

25 Aug - 26 Aug

Enjoy the city view from this stylish balcony with a sofa, chair, and table.

"Super convenient location. Lots of parking options and able to walk to all sites in this area."

฿4,982 total

includes taxes & fees

25 Aug - 26 Aug

Enjoy the city view from this balcony with a comfortable Adirondack chair and a small table.

"Great stay"

Relax in style with plush armchairs and a natural centerpiece, surrounded by a contemporary design.

"Clean, new, spacious "

฿8,346 total

includes taxes & fees

24 Aug - 25 Aug

Kitchen area with dining space, featuring a refrigerator, round table, and two chairs.

"Had a good and comfortable stay "

฿7,730 total

includes taxes & fees

12 Aug - 13 Aug

Welcome to The Neighborhood Hotel, where guests enter through a distinctive black brick facade with the hotel's name prominently displayed.

"Great suite"

Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of the city outside.

"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."

฿6,126 total

includes taxes & fees

17 Aug - 18 Aug

Two single beds with white linens, a small armchair, and a bedside table with a lamp.

"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "

฿3,099 total

includes taxes & fees

4 Aug - 5 Aug

Meetings take place around a large, rectangular table surrounded by six chairs with chrome legs.

"Great location and very clean! Will definitely be staying again. "

Enjoy meals in this cozy dining area with a long table and six chairs, surrounded by framed photographs and a potted plant.

"Excellent location and very clean! Would stay again!"

฿10,355 total

includes taxes & fees

31 Jul - 1 Aug

Enjoy a panoramic city view from this rooftop terrace, featuring a round table, wicker chairs, and a sofa with a throw blanket.

"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."

฿5,445 total

includes taxes & fees

17 Aug - 18 Aug

Relax in this stylish living space with a sofa, armchair, and dining area.

"Great location, easy stay!"

฿8,055 total

includes taxes & fees

24 Aug - 25 Aug

Situated in an urban setting, this building combines modern and traditional architectural elements.

"Its was in a good location for anyone who has family close by. Bed was wonderful. "

฿7,849 total

includes taxes & fees

4 Aug - 5 Aug

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Top Chicago Hotel Reviews

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Amazing stay at this Hotel. "

The Westin Michigan Avenue Chicago

10/10 Excellent

"We had an excellent stay at the Westin. The hotel exceeded our expectations in every way. We love the location. We’ve stayed here before and absolutely love the ability to walk to Oak St., Beach and 900 shops and so many wonderful restaurants in the area, particularly like Doc B’s. When we arrived, there was no remote for the TV in the room and the television was on. A quick call to room service and someone brought the remote up within minutes. Otherwise, the room was clean and comfortable, and even a great view. This time we had a city view last time we had a lake view they’re all great. When we checked in, I mentioned it was our 35th anniversary. The manager gave us two free drink tickets. We will definitely stay here again in fact, we just booked a night in November at the Westin and we often recommend it to many of our friends. "

Palmer House a Hilton Hotel

10/10 Excellent

"The Palmer House has many wonderful qualities to it. It’s a perfect location for those looking to explore Chicago. It’s right next to an elevated train stop and a close walk to many places. It’s a beautiful old historic hotel, incredible lobby, and for the most parts the rooms are well appointed. My room 16-179, was relatively clean… lot of smudges on the two mirrors…, the bed was very comfortable, and the amenities worked well. Perfect for a solo trip. It would not be a good room for two people or a family, seeing as it is way too small."

Find out more about Chicago

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Frequently asked questions

Can I find holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Six Flags Great America, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed art scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many holiday rentals are there in Chicago?

With 1501 Expedia holiday rentals, you're guaranteed to find just the right place for your Chicago stay.

What can I see and do in Chicago?

Cultural attractions include CIBC Theatre and Symphony Center, whereas Millennium Park and Grant Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Michigan Avenue and Navy Pier.

What are holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

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Top Holiday Rentals in Chicago

Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Gem Museum Suites

The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Kasa River North Chicago

Wrigleyville Suites

Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy Greektown Apartments

Ground Floor Studios in Chicago by 747 Lofts

Top Chicago Hotel Reviews

The Royal Sonesta Chicago Downtown

citizenM Chicago Downtown

Hyatt Regency Chicago

The Wade

The Westin Michigan Avenue Chicago

InterContinental Chicago Magnificent Mile by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

Palmer House a Hilton Hotel

Hotel Felix River North/Magnificent Mile

Find out more about Chicago

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Frequently asked questions