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Downtown Chicago, Chicago, Illinois, United States of America

Downtown Chicago holiday rentals

We found 1,235 holiday rentals — enter your dates for availability

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Find spaces that suit your style

Condos/Apartments

View 996 Condos/Apartments

Houses

View 157 Houses

Studios

View 916 Studios

Find the best place to stay — Downtown Chicago

3B/2BA Captivating Corner Apartment w/ Pier Views, Pool & Gym by ENVITAE

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 517 avg/night
(34)

3B/2.5BA Premium Luxury Penthouse | Breathtaking Views, Indoor Pool, & Gym by EN

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 693 avg/night
(19)

Sonder | The Plymouth | Classic 4BR + Gym

Sleeps 8 · 4 Bedrooms · 3 Bathrooms
AU$ 433 avg/night
(19)

Modern Chic Downtown!

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
AU$ 545 avg/night
(1)

3B/2.5BA Skyline Glass Penthouse | Breathtaking Views, Indoor Pool, & Gym by ENV

Sleeps 8 · 2 Bedrooms · 2 Bathrooms
AU$ 645 avg/night
(15)

3B/2.5BA Luxury Glass Loft | Breathtaking Views, Indoor Pool, & Gym by ENVITAE

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 641 avg/night
(9)

Search 1,235 holiday rentals

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Where to stay near Downtown Chicago?

Our 2021 accommodation listings offer a large selection of 1,235 holiday rentals near Downtown Chicago. From 996 Condos/Apartments to 157 Houses, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Downtown Chicago is on HomeAway.