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Central Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Central Chicago vacation rentals

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

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,349 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
$184 nightly
The price is $216
Oct 26 - Oct 27
Total with taxes and fees
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (49 reviews)
"Location is perfect"
United States
Mary
$240 nightly
The price is $285
Nov 1 - Nov 2
Total with taxes and fees
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (533 reviews)
"Location and facility was very nice"
United States
Brian
$278 nightly
The price is $327
Nov 1 - Nov 2
Total with taxes and fees
Level Chicago – Old Town
A modern hotel room with a bed, a desk, a chair, and a large window.

4. Trendy Gold Coast Studio Close to Downtown

Trendy Gold Coast Studio Close to Downtown
Downtown Chicago
$263 nightly
The price is $291
Oct 26 - Oct 27
Total with taxes and fees
Trendy Gold Coast Studio Close to Downtown
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

5. LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
$301 nightly
The price is $355
Oct 4 - Oct 5
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Prem Studio
A hotel room with a bed, two bedside tables, and three wall-mounted paintings.

6. Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
$277 nightly
The price is $312
Nov 2 - Nov 3
Total with taxes and fees
Stylish Japanese-Themed 2BR Apt Close to Downtown
A narrow hallway with a concrete wall, a wooden floor, a small table, and a large mirror on the right.

7. South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
$439 nightly
The price is $495
Oct 12 - Oct 13
Total with taxes and fees
South Loop Rooftop With In and Out Parking 2
A bedroom with a bed, two bedside tables, a window with a brick pattern, and a painting on the wall.

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

Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
Downtown Chicago
$388 nightly
The price is $476
Nov 3 - Nov 4
Total with taxes and fees
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
A spacious lobby with leather sofas, a coffee table, and a TV screen.

9. Downtown Chicago Stay with Free In & Out Parking 6

Downtown Chicago Stay with Free In & Out Parking 6
Downtown Chicago
$485 nightly
The price is $552
Oct 21 - Oct 22
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 6
A modern kitchen with wooden cabinets, a stainless steel dishwasher, a microwave, a coffee maker, and a toaster.

10. Smart Simple and Spacious 4BR Apt

Smart Simple and Spacious 4BR Apt
South Loop
8.2 out of 10, Very good, (13 reviews)
"Everything was exactly as described."
United States
Sydney D.
$406 nightly
The price is $444
Oct 13 - Oct 14
Total with taxes and fees
Smart Simple and Spacious 4BR Apt
A bedroom with a bed, a wardrobe, a bench, and a floor lamp.

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

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay."
United States
William H.
$786 nightly
The price is $900
Oct 21 - Oct 22
Total with taxes and fees
Wabash 4BR - Pool, Free In & Out Parking 4
A modern bedroom with a large bed, a bedside table, a lamp, and a framed abstract artwork on the wall.

12. Stylish 4BR South Loop Home

Stylish 4BR South Loop Home
Near South Side
$411 nightly
The price is $450
Oct 13 - Oct 14
Total with taxes and fees
Stylish 4BR South Loop Home
A modern kitchen with wooden cabinets, stainless steel appliances, and a white tiled backsplash.

13. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Property is new and really nice. Super clean and well put together. Would stay here again."
United States
Devin D.
$809 nightly
The price is $928
Oct 8 - Oct 9
Total with taxes and fees
Wabash 4BR - Pool, Free In & Out Parking 1
A neatly arranged bedroom with a bed, bedside table, lamp, and a wall-mounted artwork.

14. Stylish 4BR Stay-Prime Location

Stylish 4BR Stay-Prime Location
Near South Side
$411 nightly
The price is $450
Oct 13 - Oct 14
Total with taxes and fees
Stylish 4BR Stay-Prime Location
A compact laundry room with a front-loading washer and dryer, a framed picture on the wall, and a towel rack.

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

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
$536 nightly
The price is $614
Oct 7 - Oct 8
Total with taxes and fees
Plymouth Collection: 3BD 2BA High Floor with Gym
A modern living room with a sofa, a bed, a dining table, and a TV.

16. Gold Coast Hideaway | Vintage & Inviting Studio

Gold Coast Hideaway | Vintage & Inviting Studio
Downtown Chicago
$230 nightly
The price is $252
Oct 28 - Oct 29
Total with taxes and fees
Gold Coast Hideaway | Vintage & Inviting Studio
A bedroom with a bed, bedside tables, a desk, and a chair. There are windows with blinds, a ceiling fan, and a rug on the floor.

17. Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
$235 nightly
The price is $258
Oct 13 - Oct 14
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
A living room with a sofa, two armchairs, a coffee table, a wooden cabinet, and a ceiling fan.

18. Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
$309 nightly
The price is $344
Oct 26 - Oct 27
Total with taxes and fees
Stylish Gold Coast 1BR with Vintage Flair
A hotel room with a large grey sofa, a small table with a copper pot, a red lamp, and a bed with white linens.

19. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
$281 nightly
The price is $332
Oct 4 - Oct 5
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 1 BR
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

20. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
$350 nightly
The price is $413
Oct 7 - Oct 8
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Studio
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 Central Chicago Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"The room was very spacious. The location of the hotel was great. The breakfast was delicious. We will definitely stay here again!"
Samantha 1-night trip
Posted 5 hours ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Central Chicago

Everything you need to know about Central 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 Central 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 Central Chicago vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Central Chicago vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Central 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 Central 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 $216 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 Central Chicago rentals

At Expedia, we put the best Central 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 Central 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 Central 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 Central 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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