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Uptown, Chicago, Illinois, United States of America

Uptown holiday rentals

We found 1,052 holiday rentals — enter your dates for availability

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Find spaces that suit your style

Houses

View 129 Houses

Condos/Apartments

View 851 Condos/Apartments

Studios

View 793 Studios

Find the best place to stay — Uptown

Beautiful 9Br Mansion W/ 5 Parking Spots. Walk To Wrigley Field & Lake Michigan!

Sleeps 21 · 9 Bedrooms · 3 Bathrooms
AU$ 1,443 avg/night
(54)

Large Vintage 3-BR In Historic Buena Park Section Of Chicago - Great Value!!

Sleeps 8 · 3 Bedrooms · 1 Bathroom
AU$ 275 avg/night
(83)

❤️ Lowest Rates! Spacious Duplex with Free Parking!

Sleeps 9 · 4 Bedrooms · 3 Bathrooms
AU$ 452 avg/night
(7)

Spacious 3 BDRM 2.5 Bath Duplex close to Lakefront, Wrigley, and train

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
AU$ 550 avg/night
(6)

Great Location-Beautiful Friendly Andersonville Neighborhood

Sleeps 6 · 3 Bedrooms · 1 Bathroom
AU$ 270 avg/night
(121)

❤️ Spacious and Airy Apartment Big Groups!

Sleeps 5 · 3 Bedrooms · 2 Bathrooms
AU$ 364 avg/night
(6)

Search 1,052 holiday rentals

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Where to stay near Uptown?

Our 2021 accommodation listings offer a large selection of 1,052 holiday rentals near Uptown. From 129 Houses to 851 Condos/Apartments, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Uptown for a long holiday or a weekend break is on HomeAway.

Can I rent Houses in Uptown?

Yes, of course. HomeAway.com.au offers 129 Houses in Uptown. Our other popular types of Uptown holiday rentals include:

  • Condos/Apartments: 851 holiday houses
  • Studios: 793 holiday houses
  • Townhouses: 12 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals including Hotels and more.

Can I find a holiday accommodation with pool in Uptown?

Yes, you can select your preferred holiday accommodation with pool among our 191 holiday homes with pool available in Uptown. Please use our search bar to access the selection of holiday rentals available.