Chicago Vacation Rentals from $106: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Chicago?

Clarendon Hills Top Floor : This highly rated vacation home rental in Chicago is equipped with a barbecue grill, air-conditioning, and free WiFi to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Chicago are Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed and Lincoln Park Living - Suite 2! .

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Vacation Rentals in Chicago

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

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

$194 nightly

Aug 4 - Aug 5

Total includes taxes and fees

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

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

$127 nightly

Aug 17 - Aug 18

Total includes taxes and fees

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

"Hotel was nice"

$240 nightly

Aug 27 - Aug 28

Total includes taxes and fees

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. "

$150 nightly

Aug 25 - Aug 26

Total includes taxes and fees

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."

$131 nightly

Aug 25 - Aug 26

Total includes taxes and fees

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 "

$219 nightly

Aug 24 - Aug 25

Total includes taxes and fees

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

"Had a good and comfortable stay "

$208 nightly

Aug 12 - Aug 13

Total includes taxes and fees

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."

$161 nightly

Aug 17 - Aug 18

Total includes taxes and fees

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. "

$94 nightly

Jul 30 - Jul 31

Total includes taxes and fees

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. "

$302 nightly

Aug 14 - Aug 15

Total includes taxes and fees

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!"

$270 nightly

Jul 31 - Aug 1

Total includes taxes and fees

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."

$135 nightly

Aug 17 - Aug 18

Total includes taxes and fees

$205 nightly

Aug 11 - Aug 12

Total includes taxes and fees

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

"Great location, easy stay!"

$212 nightly

Aug 24 - Aug 25

Total includes taxes and fees

Relax in comfort with a large bed, featuring a dark headboard and crisp white bedding, and a cozy throw blanket.

$185 nightly

Aug 5 - Aug 6

Total includes taxes and fees

Enjoy cooking and entertaining in this well-equipped kitchen with stainless steel appliances and sleek cabinetry.

"Great place! 15 min walk to Wrigley "

$185 nightly

Aug 5 - Aug 6

Total includes taxes and fees

Restful retreat with a neatly made bed and a bedside lamp.

$239 nightly

Aug 12 - Aug 13

Total includes taxes and fees

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Top Chicago Hotel Reviews

Hotel Felix River North/Magnificent Mile

10/10 Excellent

"Great hotel ! "

Swissotel - Chicago

10/10 Excellent

"I love it!!!! Everything, once you enter it smells like a spa, everything so clean, so beautiful. Amuse is an excellent option to a light breakfast, lunch or dinner. The elevators were fast, the gym was complete with a lounge space… just beautiful. Our room was very spacious and with a million dollar view to the Navy Pier. The housekeeper just did an excellent job taking care of our room. This was a mother-daughter trip and I recommend this hotel 200%. "

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable. The property is very nice, although we didn't get the two beds that we selected through Orbitz. The hotel is on the red line, so not as convenient to the airport as a hotel on the blue line. Parking here is pricey. If you stay here, Hendrickx Belgian Belgian Bread Crafter is around the corner and an absolute must visit. Wildberry is on the other side and also very good. The Hancock Building is a two minute walk. If you love city views, the 360 experience is worth a visit, and is less crowded than the Willis Tower. We did the Tilt experience and it was not worth the money. If you go to Chicago and haven't gone on an architectural boat tour, this is an absolute MUST. Be sure to choose a tour affiliated with the Chicago Architectural Center because that's a nonprofit worth supporting AND the guides are amazing. It's a 20 minute walk from the hotel and you walk along MichiganAve., which rivals Fifth Avenue in New York for window shopping, retail, artwork, and restaurants. Love, love, love Chicago and would stay at this property again."

Congress Plaza Hotel

10/10 Excellent

"There are areas of the property outside that need some tlc. The hallways are outdated in decor but the room was clean and comfortable. The reception area was very pretty. The staff was courteous and friendly. The hotel itself has a good location walkable to the Soldier Field which we were in town for a concert there. There are walkable restaurants and parks nearby. We did not feel unsafe in the area. "

Price trends for vacation rentals in Chicago

Less expensive	More expensive	Next month
January	July	$378

Month	Price
January	$180
February	$209
March	$239
April	$222
May	$276
June	$240
July	$499
August	$378
September	$409
October	$359
November	$285
December	$260

Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Chicago. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Chicago

Everything you need to know about Chicago vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chicago vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chicago vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chicago vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chicago. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chicago in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $106 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chicago rentals

At Expedia, we put the best Chicago vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chicago rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chicago vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chicago. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want 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.

What are some of the best vacation rentals in Chicago?

Clarendon Hills Top Floor: This highly rated vacation home rental in Chicago is equipped with a barbecue grill, air-conditioning, and free WiFi to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Chicago are Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed and Lincoln Park Living - Suite 2!.

How many vacation rentals are there in Chicago?

With 1501 Expedia vacation rentals, you're sure 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 vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.

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Chicago Vacation Rentals

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Vacation Rentals in Chicago

Sentral Michigan Avenue

Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

Level Chicago – Old Town

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Kasa South Loop Chicago

Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Gem Museum Suites

The Gem Museum Suites

The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

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

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

Kasa River North Chicago

Kasa River North Chicago

Wrigleyville Suites

Wrigleyville Suites

Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy The Opal Apartments River North

Lakeview 2BR Apartment

Lakeview 2BR Apartment

Sonder by Marriott Bonvoy Greektown Apartments

Sonder by Marriott Bonvoy Greektown Apartments

Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt

Cozy, Fully Set-Up 1BR Space

Cozy, Fully Set-Up 1BR Space

Huge Projector and Designated Workspace - Near Wrigley!

Huge Projector and Designated Workspace - Near Wrigley!

Top Chicago Hotel Reviews

Hotel Felix River North/Magnificent Mile

Price trends for vacation rentals in Chicago

Price trends for vacation rentals in Chicago

Find out more about Chicago

Find out more about Chicago

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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