Chicago Vacation Rentals from ￥12,915: Search Short-Term Rentals

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

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line : This highly rated vacation home rental in Chicago is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. 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 Sleeps 18 • 8BR • Game Room • Gym • Theater and LUXE 3 BR, 2 BA + Hot Tub .

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Our top choices for Chicago vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Downtown Chicago

Jacob

￥26,564 total

includes taxes & fees

Nov 9 - Nov 10

2. Kasa Lake Shore Chicago

Downtown Chicago

Iliana

￥36,484 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Downtown Chicago

Kerry

￥52,169 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

4. LIVN Millennium Park Downtown Chicago 2BR

Downtown Chicago

Granada

￥73,392 total

includes taxes & fees

Oct 21 - Oct 22

A waiting area with two white chairs, a white table, a television mounted on the wall, and an exit door.

5. Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago

Eric Dallas

￥75,713 total

includes taxes & fees

Nov 9 - Nov 10

A modern room with a sofa, a dining table, and a window with a view of buildings.

6. LIVN West Loop Chicago 2 BR City View

Downtown Chicago

duane

￥79,907 total

includes taxes & fees

Oct 18 - Oct 19

A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

7. Chic Urban Retreat Near Wrigley Field w/Parking

Lakeview

Bridget

￥33,376 total

includes taxes & fees

Nov 2 - Nov 3

A compact laundry room with a front-loading washer and dryer, a framed picture on the wall, and a towel rack.

8. Plymouth Collection: 3BD 2BA High Floor with Gym

Downtown Chicago

Derek M.

A gym with weightlifting equipment, benches, and a mirrored wall.

9. South Loop Rooftop With In & Out Parking 1

Downtown Chicago

Shayla S.

A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

10. River North Rooftop With In and Out Parking 3

Downtown Chicago

Kara B.

A neatly made bed with white bedding, two bedside tables with lamps, and a single decorative pillow.

11. Wabash 4BR - Pool, Free In & Out Parking 2

Downtown Chicago

Diana Sofia B.

￥144,002 total

includes taxes & fees

Oct 22 - Oct 23

A room with a skylight, a mounted TV, and a door.

12. Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants

Downtown Chicago

￥90,230 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

13. 2BR Apt with 2 Baths & Laundry

Near West Side

michele

￥39,870 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

14. 3BR Complete and Spacious Apartment in Ideal Spot

West Town

Francis

￥41,848 total

includes taxes & fees

Oct 26 - Oct 27

A rooftop terrace with a fire pit, seating area, and a city skyline view.

15. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

West Town

Jay J.

￥37,634 total

includes taxes & fees

Nov 4 - Nov 5

A bedroom with a bed, bedside tables, a ceiling fan, framed pictures, and a window.

16. Stylish Gold Coast 1BR with Vintage Flair

Downtown Chicago

￥53,581 total

includes taxes & fees

Oct 28 - Oct 29

A modern living room with large windows, a flat-screen TV, a sofa, a coffee table, and a dining area with stools and a small table.

17. Modern West Loop Gem-City Views & Prime Location 6

Downtown Chicago

Tom S.

￥152,314 total

includes taxes & fees

Oct 28 - Oct 29

A modern bedroom with a bed, a sofa, and a hanging plant.

18. Cozy studio in Andersonville Chicago

Edgewater

Sherry M.

￥22,045 total

includes taxes & fees

Nov 2 - Nov 3

A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

19. Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Lakeview

Kate P.

￥173,159 total

includes taxes & fees

Oct 19 - Oct 20

A bedroom with a large bed, a bedside table, a nightstand, a window with blinds, and a wall-mounted artwork.

20. Comfortable 3BR/2BA Haven | Ideal for Families

Avondale

Marc

￥39,587 total

includes taxes & fees

Oct 18 - Oct 19

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Top Chicago Hotel Reviews

Hyatt Regency Chicago

10/10 Excellent

"."

Congress Plaza Hotel

10/10 Excellent

"We stayed at the Congress for a Bears game. We selected it based on price and proximity to Soldier Field. The price was incredibly reasonable, so I was a bit concerned about the quality and cleanliness of the room and hotel prior to checking in. We were more than pleased with our room and the hotel overall and feel it was great value for our money. The room was very clean and had been updated quite recently. It was roomie in both the room itself and the bathroom. We also appreciated the amenities in the room, including a coffee maker, refrigerator, a large, walk-in closet, plenty of drawer storage for clothes and extra seating and table. It is also near do much in the city, so it’s a great place to stay. The only issue that I had is I wish the TV had been a bit larger. But other than that, I would highly recommend the Congress."

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The hotel is in a great location. The room was decent and so was the breakfast. We were entitled to vouchers for breakfast, cocktails and dinner as well as water bottles. At check-in, it would have been nice to be told that and get those vouchers. We had to ask for them the next day after reading a message received from the hotel. It would be nice also at check-in to let us know that housekeeping is every other day. Overall we still had a good stay."

Find out more about Chicago

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Flights to Chicago

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 theater 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated vacation home rental in Chicago is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. 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 Sleeps 18 • 8BR • Game Room • Gym • Theater and LUXE 3 BR, 2 BA + Hot Tub.

How many vacation rentals are there in Chicago?

With 933 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 Soldier Field 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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Check prices for these dates

Our top choices for Chicago vacation rentals

1. Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

3. Level Chicago – Old Town

4. LIVN Millennium Park Downtown Chicago 2BR

5. Downtown Chicago Stay with Free In & Out Parking 3

6. LIVN West Loop Chicago 2 BR City View

7. Chic Urban Retreat Near Wrigley Field w/Parking

8. Plymouth Collection: 3BD 2BA High Floor with Gym

9. South Loop Rooftop With In & Out Parking 1

10. River North Rooftop With In and Out Parking 3

11. Wabash 4BR - Pool, Free In & Out Parking 2

12. Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants

13. 2BR Apt with 2 Baths & Laundry

14. 3BR Complete and Spacious Apartment in Ideal Spot

15. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

16. Stylish Gold Coast 1BR with Vintage Flair

17. Modern West Loop Gem-City Views & Prime Location 6

18. Cozy studio in Andersonville Chicago

19. Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

20. Comfortable 3BR/2BA Haven | Ideal for Families

Find vacation rentals that suit your style

Top Chicago Hotel Reviews

Hyatt Regency Chicago

Congress Plaza Hotel

The Chicago Hotel Collection Ambassador Gold Coast

Fairmont Chicago at Millennium Park

The Godfrey Hotel Chicago

Freehand Chicago

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Find out more about Chicago

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