Apartment vacation rentals in Downtown Chicago
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Downtown Chicago
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago apartment rentals
Weekly apartment rentals
Apartment in Humboldt Park
4.98 out of 5 average rating, 109 reviewsHumboldt Park Loft
Apartment in Irving Park
4.87 out of 5 average rating, 104 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Portage Park
4.95 out of 5 average rating, 111 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Apartment in Chicago
4.82 out of 5 average rating, 273 reviews*Entire City Apartment 1 block to Train Park Free
Apartment in Chicago
4.84 out of 5 average rating, 131 reviewsPerfect Private Getaway in Perfect Pilsen
Apartment in Chicago
4.96 out of 5 average rating, 376 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 244 reviewsModern
Private apartment rentals
Apartment in Oak Park
4.89 out of 5 average rating, 338 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Apartment in Lincoln Park
4.79 out of 5 average rating, 135 reviewsRoomy Getaway in Vibrant Center of Lincoln Park
Apartment in Bridgeport
4.98 out of 5 average rating, 171 reviewsBridgeport Garden Apartment
Apartment in Lincoln Square
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Apartment in Chicago
4.99 out of 5 average rating, 196 reviewsExplore Lincoln Park from a Polished Apartment
Apartment in Chicago
4.98 out of 5 average rating, 132 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in Chicago
4.79 out of 5 average rating, 19 reviewsCozy Condo near Downtown Chicago
Apartment in Chicago
4.89 out of 5 average rating, 94 reviewsMcCormick 2B/2Ba for up to 6 guests w Opt Parking
Apartment rentals with a hot tub
Apartment in Near South Side
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Town
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 205 reviews“Dream slice of urban homesteading.”
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Logan Square
4.91 out of 5 average rating, 33 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in West Rogers Park
4.82 out of 5 average rating, 22 reviewsSpacious Beautiful Condo
Apartment in Magnificent Mile
4.87 out of 5 average rating, 77 reviews4Br Gold Coast Duplex w Jacuzzi in the Bedroom!
Destinations to explore
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Serviced apartment rentals United States
- Apartment rentals United States
- Apartment rentals Chicago
- Rentals with breakfast Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a washer and dryer Downtown Chicago
- Beachfront rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- House rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Hotel rentals Downtown Chicago
- Condo rentals Downtown Chicago
- Rentals with a home theater Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with beach access Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Lake Geneva
- Apartment rentals Illinois
- Apartment rentals Cook County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes