Chicago Riverwalk showing a city, a river or creek and a ferry

Holiday rentals near Chicago Riverwalk

We found 3,177 holiday rentals — enter your dates for availability

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February 2026

March 2026

Take a look at holiday rentals close to Chicago Riverwalk that provide the perfect home base for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you need and want for your stay, which might include air conditioning and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Chicago Riverwalk

Showing deals for:8 May - 15 May

Wonderful

(63 reviews)

Heart of the City Group Hub • Patio • Fireplace • Parking

Chicago

7% off

for 7 nights, 1 home

AU$916 per night

includes taxes & fees

Spacious living room with a lot of daylight and large windows.

Wonderful

(10 reviews)

Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums

Chicago

11% off

for 7 nights, 1 apartment

AU$643 per night

includes taxes & fees

Excellent

(15 reviews)

Brand New 3BR/2BA • Washer/Dryer • 5 Min to Downtown

Chicago

8% off

for 7 nights, 1 apartment

AU$381 per night

includes taxes & fees

Wonderful

(15 reviews)

Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking

Chicago

15% off

for 7 nights, 1 apartment

AU$531 per night

includes taxes & fees

Excellent

(11 reviews)

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

7% off

for 7 nights, 1 home

AU$1,314 per night

includes taxes & fees

Wonderful

(21 reviews)

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Chicago

7% off

for 7 nights, 1 home

AU$1,232 per night

includes taxes & fees

Open living room features vaulted ceilings and hardwood floors.

Exceptional

(28 reviews)

Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

Chicago

7% off

for 7 nights, 1 apartment

AU$436 per night

includes taxes & fees

Exceptional

(87 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off

for 7 nights, 1 home

AU$1,303 per night

includes taxes & fees

Exceptional

(8 reviews)

Archer #2 | New 3 Bedroom near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off

for 7 nights, 1 apartment

AU$516 per night

includes taxes & fees

Wonderful

(13 reviews)

4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off

for 7 nights, 1 home

AU$722 per night

includes taxes & fees

Excellent

(20 reviews)

Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.

Chicago

7% off

for 7 nights, 1 apartment

AU$312 per night

includes taxes & fees

Exceptional

(26 reviews)

First floor of Historic Oak Park Villa, Grge:2Cars

Oak Park

12% off

for 7 nights, 1 apartment

AU$367 per night

includes taxes & fees

Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.

Exceptional

(72 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off

for 7 nights, 1 home

AU$1,444 per night

includes taxes & fees

Exceptional

(40 reviews)

Lincoln Square Oasis - Bright, Clean and in Great Location

Chicago

7% off

for 7 nights, 1 apartment

AU$339 per night

includes taxes & fees

Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc

Exceptional

(15 reviews)

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off

for 7 nights, 1 apartment

AU$394 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find properties near top attractions in Chicago Riverwalk

Chicago Riverwalk

Find the best place to stay - Chicago Riverwalk

Level Chicago – Old Town

Sleeps 4

Premier Host

Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly

Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host

Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile

Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Sleeps 8 · 4 bedrooms · 2 bathrooms

Top rated rentals - Chicago Riverwalk

Premier Host

Fabulous

The property is a fully equipped home, has everything you need and makes life simple while you are there. The owner is also right next door and very responsive, friendly and helpful. Taylor street is a very short walk away, the pink line is a short walk away, great location, very quiet.

Robin N.

Stayed July 2024

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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value