Vacation Rentals in Chicago, IL
· House in Lakeview
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
4 Beds · 5 baths · Sleeps 10 ·
Ceiling Fan · Fitness Center · Walk In Closets ·
From
$1,095/nightAmenities
Ceiling Fan
Fitness Center
Walk In Closets
Fireplace
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Other spaces
Kitchen
· Condo in Armour Square
Charming 3b/1.5ba Chinatown Home by McCormick★Downtown
3 Beds · 2 baths ·
Oven · In Unit Laundry · Kitchen ·
From
$140/nightAmenities
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Portage Park
P2N Stylishly Furnished Studio Apt in Portage Park
Studio · 1 bath ·
Hardwood Floor · Dishwasher · Oven ·
From
$202/nightAmenities
Hardwood Floor
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Lincoln Square
CB3 Deluxe 1BR Apt in a Ravenswood
1 Bed · 1 bath ·
Hardwood Floor · Dishwasher · Oven ·
From
$267/nightAmenities
Hardwood Floor
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Near North Side
57 BLDG Luxury Building in Gold Coast - 3 full apartments!
Studio · 4 baths · Sleeps 24 ·
Dishwasher · Oven · In Unit Laundry ·
From
$1,233/nightAmenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Lincoln Park
Lincoln Park, Zoo, Lake | Easy Access | Zencity
2 Beds · 2 baths · Sleeps 4 ·
High Ceilings · Lake · Waterfront ·
From
$219/nightAmenities
High Ceilings
Lake
Waterfront
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Lincoln Park
Charming 2 Bedroom Flat in heart of Lincoln Park
2 Beds · 1 bath · Sleeps 4 ·
Balcony · Dishwasher · Oven ·
From
$412/nightAmenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Garage Parking
Other spaces
Balcony, Kitchen
· Hotel in Near North Side
The Ritz-Carlton, Chicago
1 Bed · Sleeps 4 ·
Smoking Allowed · Hot Tub · Pool ·
From
$471/nightAmenities
Smoking Allowed
Hot Tub
Pool
Carpet
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Other spaces
Workspace
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· Apartment in South Loop
McCormick Place modern 420 friendly 2br-2ba loft in Downtown Chicago Michigan avenue for 6 guests
2 Beds · 2 baths · Sleeps 6 ·
Hardwood Floor · Assigned Parking · Dishwasher ·
From
$355/nightAmenities
Hardwood Floor
Assigned Parking
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
· Hotel in Near North Side
Hotel Felix
1 Bed · Sleeps 4 ·
Smoking Allowed · Carpet · Workspace ·
From
$192/nightAmenities
Smoking Allowed
Carpet
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Concierge Service
Other spaces
Workspace
· Hotel in Near North Side
Sheraton Grand Chicago Riverwalk
1 Bed · Sleeps 5 ·
Pool · Outdoor Space · Carpet ·
From
$188/nightAmenities
Pool
Carpet
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
· Hotel in South Loop
Marriott Marquis Chicago
1 Bed · Sleeps 4 ·
Beach · Carpet · Free Parking ·
From
$175/nightAmenities
Beach
Carpet
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
· Hotel in Near North Side
The Westin Michigan Avenue Chicago
1 Bed · Sleeps 4 ·
Beach · Carpet · Free Parking ·
From
$144/nightAmenities
Beach
Carpet
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
· Hotel in Near North Side
Four Seasons Chicago
1 Bed · Sleeps 4 ·
Pool · Carpet · Assigned Parking ·
From
$458/nightAmenities
Pool
Carpet
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Concierge Service
Other spaces
Workspace
· Hotel in Loop
The Palmer House Hilton
1 Bed · Sleeps 4 ·
Pool · Carpet · Free Parking ·
From
$196/nightAmenities
Pool
Carpet
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
· Hotel in Near North Side
Ambassador Chicago, part of JdV by Hyatt
1 Bed · 1 bath · Sleeps 4 ·
Smoking Allowed · Carpet · Free Parking ·
From
$196/nightAmenities
Smoking Allowed
Carpet
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
· Hotel in Near North Side
Sable At Navy Pier Chicago, Curio Collection By Hilton
1 Bed · Sleeps 4 ·
Outdoor Space · Carpet · Free Parking ·
From
$357/nightAmenities
Carpet
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Concierge Service
Other spaces
Workspace
· Hotel in Loop
Chicago Athletic Association, part of Hyatt
1 Bed · Sleeps 4 ·
Assigned Parking · Workspace · On Site Laundry ·
From
$207/nightAmenities
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Concierge Service
Fitness Center
Dry Cleaning Service
Other spaces
Workspace
· Hotel in Loop
Hilton Chicago
1 Bed · Sleeps 6 ·
Hot Tub · Pool · Outdoor Space ·
From
$182/nightAmenities
Hot Tub
Pool
Carpet
Free Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
· Hotel in Loop
Pendry Chicago
1 Bed · Sleeps 4 ·
Smoking Allowed · Free Parking · Assigned Parking ·
From
$230/nightAmenities
Smoking Allowed
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Concierge Service
Other spaces
Workspace
· Hotel in Loop
Cambria Hotel Chicago Loop/Theatre District
1 Bed · Sleeps 5 ·
Hardwood Floor · Free Parking · Assigned Parking ·
From
$189/nightAmenities
Hardwood Floor
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Concierge Service
Other spaces
Workspace
· Apartment in Lincoln Park
Flat in Lincoln Park 2-Flat Central to Everything
2 Beds · 2 baths · Sleeps 4 ·
Balcony · Free Parking · Assigned Parking ·
From
$357/nightAmenities
Free Parking
Assigned Parking
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Workspace, Kitchen
· Apartment in South Shore
Modern Chicago Condo about 9 Miles to Downtown!
4 Beds · 2 baths · Sleeps 8 ·
Hot Tub · Oven · In Unit Laundry ·
From
$251/nightAmenities
Hot Tub
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Irving Park
Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking
1 Bed · 1 bath · Sleeps 3 ·
Balcony · Outdoor Space · Free Parking ·
From
$131/nightAmenities
Free Parking
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
· Apartment in North Lawndale
Large 6 Bedroom House 4 Parking Downtown 15min
6 Beds · 3 baths · Sleeps 15 ·
Fireplace · Balcony · Outdoor Space ·
From
$411/nightAmenities
Fireplace
Hardwood Floor
Free Parking
Assigned Parking
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Other spaces
Balcony, Workspace, Kitchen
· Apartment in Near North Side
Cloud9 - River North at Aurelien
2 Beds · 2 baths · Sleeps 6 ·
Private Pool · Fireplace · Pool ·
From
$602/nightAmenities
Private Pool
Fireplace
Pool
Assigned Parking
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Kitchen
· Apartment in Lakeview
2 Bed Apt w/ Office, Free Parking, Near Wrigley
2 Beds · 1 bath · Sleeps 4 ·
Fireplace · Free Parking · Dishwasher ·
From
$277/nightAmenities
Fireplace
Free Parking
Dishwasher
Oven
Air Conditioning
Furnished
Wifi
Storage
Other spaces
Workspace, Kitchen
· Apartment in Near North Side
Sonder The Opal
3 Beds · 2 baths · Sleeps 6 ·
Dishwasher · Workspace · Oven ·
From
$260/nightAmenities
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Elevator
Other spaces
Workspace, Kitchen
· Apartment in Loop
Sentral Michigan Avenue
1 Bed · 1 bath · Sleeps 4 ·
Hot Tub · Fireplace · Pool ·
From
$161/nightAmenities
Hot Tub
Fireplace
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
· Apartment in South Loop
Cool South Loop Loft 5 Min to McCormick & Loop
2 Beds · 1 bath · Sleeps 3 ·
Carpet · Hardwood Floor · Dishwasher ·
From
$208/nightAmenities
Carpet
Hardwood Floor
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Apartment in Chatham
Charming Chicago Apartment Less Than 9 Mi to Dtwn!
4 Beds · 2 baths · Sleeps 10 ·
Free Parking · Dishwasher · Oven ·
From
$406/nightAmenities
Free Parking
Dishwasher
Oven
Furnished
Wifi
Other spaces
Kitchen
· Apartment in South Loop
McCormick Place 3BR-2BA unit with Optional Parking - sleeps 8
3 Beds · 2 baths · Sleeps 8 ·
Carpet · Hardwood Floor · Assigned Parking ·
From
$447/nightAmenities
Carpet
Hardwood Floor
Assigned Parking
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Other spaces
Workspace, Kitchen
· Apartment in South Loop
McCormick Place 2b/2b with optional parking and Gym/sleeps 6
2 Beds · 2 baths · Sleeps 6 ·
Dishwasher · Workspace · Oven ·
From
$355/nightAmenities
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Storage
Other spaces
Workspace, Kitchen
· Apartment in South Loop
McCormick Place beautiful 3b/2b with Patio and skyline view and Parking
3 Beds · 2 baths · Sleeps 6 ·
Balcony · Outdoor Space · Carpet ·
From
$607/nightAmenities
Carpet
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Workspace, Kitchen
· Apartment in South Loop
McCormick Place 3BR-2BA with Optional Parking - sleeps 8
3 Beds · 2 baths · Sleeps 8 ·
Carpet · Hardwood Floor · Assigned Parking ·
From
$526/nightAmenities
Carpet
Hardwood Floor
Assigned Parking
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Other spaces
Workspace, Kitchen
· Apartment in South Loop
McCormick place fabulous 420 friendly 2br/2ba with optional parking/sleeps 6
2 Beds · 2 baths · Sleeps 6 ·
Dishwasher · Workspace · Oven ·
From
$394/nightAmenities
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Storage
Other spaces
Workspace, Kitchen
· Apartment in South Loop
McCormick Place magnificent 2br-2ba with Parking, Patio, Gym, sleeps 6
2 Beds · 2 baths · Sleeps 6 ·
Outdoor Space · Hardwood Floor · Assigned Parking ·
From
$444/nightAmenities
Hardwood Floor
Assigned Parking
Dishwasher
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Apartment in South Loop
McCormick Place 2br-2ba with Optional Parking,Patio,Gym for 6 guests
2 Beds · 2 baths · Sleeps 6 ·
Outdoor Space · Hardwood Floor · Assigned Parking ·
From
$444/nightAmenities
Hardwood Floor
Assigned Parking
Dishwasher
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Apartment in South Loop
McCormick Place Skyline view 2br-2ba with parking for 6 guests
2 Beds · 2 baths · Sleeps 6 ·
Hardwood Floor · Assigned Parking · Dishwasher ·
From
$394/nightAmenities
Hardwood Floor
Assigned Parking
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
· Apartment in South Loop
McCormick Place 2br-2ba with Parking, Patio, Gym for 6 guests
2 Beds · 2 baths · Sleeps 6 ·
Outdoor Space · Hardwood Floor · Assigned Parking ·
From
$444/nightAmenities
Hardwood Floor
Assigned Parking
Dishwasher
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Hotel in West Town
747 Lofts by RedAwning - Ground Floor Studios in Chicago
1 Bed · 1 bath · Sleeps 3 ·
Oven · In Unit Laundry · Kitchen ·
From
$105/nightAmenities
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Hotel in West Town
747 Lofts by RedAwning - Chicago Second Floor Studio
1 Bed · 1 bath · Sleeps 2 ·
Dishwasher · Oven · In Unit Laundry ·
From
$106/nightAmenities
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Hotel in West Town
747 Lofts by RedAwning - Chicago Third Floor Studio
1 Bed · 1 bath · Sleeps 3 ·
Dishwasher · Oven · In Unit Laundry ·
From
$113/nightAmenities
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Hotel in West Town
747 Lofts by RedAwning - River West, Third Floor Chicago
1 Bed · 1 bath · Sleeps 3 ·
Dishwasher · Oven · In Unit Laundry ·
From
$105/nightAmenities
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Roseland
Chicago Home with Spacious Yard 14 Mi to Dtwn
2 Beds · 2 baths · Sleeps 4 ·
Free Parking · Dishwasher · Oven ·
From
$158/nightAmenities
Free Parking
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Hotel in Near North Side
Kasa River North Chicago
1 Bed · 1 bath · Sleeps 5 ·
Pool · Dishwasher · Workspace ·
From
$138/nightAmenities
Pool
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Apartment in North Lawndale
5BR newly remodeled in a historical street sleeps11 Free Parking
5 Beds · 2 baths · Sleeps 10 ·
Outdoor Space · Hardwood Floor · Free Parking ·
From
$353/nightAmenities
Hardwood Floor
Free Parking
Assigned Parking
Dishwasher
Oven
On Site Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Hotel in West Town
747 Lofts by RedAwning - River West, Second Floor Chicago
1 Bed · 1 bath · Sleeps 3 ·
Dishwasher · Oven · In Unit Laundry ·
From
$107/nightAmenities
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· Hotel in Loop
The LaSalle Chicago, Autograph Collection
1 Bed · Sleeps 4 ·
Hardwood Floor · Free Parking · Assigned Parking ·
From
$299/nightAmenities
Hardwood Floor
Free Parking
Assigned Parking
On Site Laundry
Air Conditioning
Furnished
Wifi
Concierge Service
Other spaces
Workspace
· Apartment in South Loop
McCormick Place Spacious family heaven 3b/2b with optional parking that sleeps up to 8
3 Beds · 2 baths · Sleeps 8 ·
Hardwood Floor · Assigned Parking · Dishwasher ·
From
$570/nightAmenities
Hardwood Floor
Assigned Parking
Dishwasher
Oven
In Unit Laundry
On Site Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Showing 1 - 50 of 2,153 results
Updated: March 14, 2023
Learn about vacation rentals in
Chicago
Chicago, IL, is an expansive city located against the edge of Lake Michigan. From the beaches along the lakefront, to the upscale shopping on Michigan Avenue, there’s something for everyone in Chicago. The Loop is home to many theaters that feature both Broadway plays and independent productions. Navy Pier is where visitors can find carnival rides, a gigantic Ferris wheel, live theater performances, and a plethora of dining options. Just to the north of downtown is the oldest free zoo in the nation, the Lincoln Park Zoo, a coveted Chicago attraction for families.
Chicago, Illinois: What to know before you go
Chicago is a city that's known for experiencing all four seasons, sometimes on the same day. If you're visiting during the late fall to early spring, bring clothes that you can layer. The summer tends to be hot, humid, and rainy. Most of Chicago's attractions are located along the lakefront, downtown, and the River North district. Public transportation reaches all of these areas, but taxis and shuttles are also plentiful. The off-season starts in late October and goes through late May, although the holiday season is popular for tourism.
Getting around Chicago
Walking
7/10
Grab your reusable bags–many shops and stores are within walking distance.
Car
7/10
This area is close to freeways and has adequate parking options.
Transit
7/10
Popular public transit options are just a short walk from this location.
Points of interest in Chicago
Groceries
8/10
At least one grocery store within a 15-minute walk
Shopping
6/10
Variety of shops within walking distance
Cafes
5/10
Some cafés within walking distance
Restaurants
6/10
Variety of restaurants within walking distance
Parks
8/10
Large amount of park space nearby
Nightlife
4/10
Some bars within walking distance
Vacation Rentals in Chicago, IL FAQ
How many vacation rentals in Chicago are available?
There are currently 2571 vacation rentals in Chicago available. Our vacation rentals in Chicago include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Chicago?
Yes, right now there are 1375 pet friendly vacation rentals in Chicago. A pet friendly vacation rental in Chicago means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Chicago with a pool?
Yes there are vacation rentals with a pool available in Chicago, IL. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Chicago with internet access?
As of March 14, 2023, there are vacation rentals with internet access available in Chicago, Illinois. Check out more enjoyable destinations on Vacations by Zumper.
