Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans! 
Best Price Match
8.8 (342 Reviews) Apartment
Apartments • Free WiFi • Private bathroom
Best Price Match Uptown Vacation Rentals & NearbyHoliday Homes
Find Vacation Rentals in or near Uptown. Find vacation rentals in Uptown, Chicago.
The Avondale Guesthouse Best Price Match
9.5 (126 Reviews) Holiday_home
The entire place is yours • 167 m² size • Free parking
Best Price Match 
2 Bed Apt w/ Office, Free Parking, Near Wrigley Best Price Match
8.8 (65 Reviews) Apartment
The entire place is yours • 111 m² size • Kitchen
Best Price Match 
Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find Best Price Match
9.5 (43 Reviews) Holiday_home
The entire place is yours • 149 m² size • Free on-site parking
Chicago Lincoln Square • In Uptown · 3.8km to center
Best Price Match 
Stylish 2BR Pad with Up-to-date Comforts - Halsted rep Best Price Match
8.7 (17 Reviews) Apartment
The entire place is yours • 84 m² size • Pet friendly
Best Price Match 
1 Bedroom with Rooftop and Wrigley Views Best Price Match
8.8 (5 Reviews) Apartment
The entire place is yours • 800 m² size • Balcony
Best Price Match 
Stylish and Expansive 2BR Apt with Balcony - Buckingham 3 Best Price Match
7.1 (11 Reviews) Apartment
The entire place is yours • Pet friendly • Free WiFi
Best Price Match 
Spacious Historic Apartments In Lakeview Chicago - Walk to Wrigley, Nightlife, Shops, Hospitals Best Price Match
8.8 (25 Reviews) Apartment
Apartments • Free WiFi • Private bathroom
Best Price Match 
3BR Spacious Apartment with In-Unit Laundry - Kedzie 3F Best Price Match
9.0 (4 Reviews) Apartment
The entire place is yours • 102 m² size • Kitchen
Chicago Albany Park • In Uptown · 4.4km to center
Best Price Match 
Inspiring Grotto Sleeps 10-20 Free TV & Parking Best Price Match
9.3 (3 Reviews) Apartment
The entire place is yours • 186 m² size • Free on-site parking
Best Price Match 
Lincoln Park 3 BR Penthouse Best Price Match
9.3 (112 Reviews) Apartment
The entire place is yours • 165 m² size • Private parking
Chicago Lincoln Park • In Uptown · 4.0km to center
Best Price Match 
Chicago Charm Best Price Match
9.7 (70 Reviews) Apartment
The entire place is yours • 125 m² size • Kitchen
Chicago West Ridge • In Uptown · 4.0km to center
Best Price Match 
Wrigley Oasis! Steps from the Field! - 3BD 1BA Best Price Match
9.6 (34 Reviews) Apartment
The entire place is yours • 111 m² size • Free parking
Best Price Match 
Lincoln Park Living - 3 Queen Beds - Sleeps 6 Best Price Match
9.1 (40 Reviews) Holiday_home
The entire place is yours • 93 m² size • Free parking
Chicago Lincoln Park • In Uptown · 3.7km to center
Best Price Match 
Lincoln Park Apartment with Backyard! Best Price Match
8.4 (43 Reviews) Apartment
The entire place is yours • 84 m² size • Free parking
Chicago Lincoln Park • In Uptown · 4.1km to center
Best Price Match 
Lincoln Park Living - Suite 1 Best Price Match
8.7 (37 Reviews) Holiday_home
The entire place is yours • 111 m² size • Free parking
Chicago Lincoln Park • In Uptown · 3.7km to center
Best Price Match 
1BR Stylish Apartment, Perfect for Getaway - Oakdale 201 Best Price Match
8.9 (27 Reviews) Apartment
The entire place is yours • 500 m² size • Pet friendly
Best Price Match 
Chic & Updated Studio Apt in East Lakeview - Barry S1 Best Price Match
8.4 (37 Reviews) Apartment
The entire place is yours • 31 m² size • Kitchen
Best Price Match 
Hollywood Rentals LLC Best Price Match
5.6 (385 Reviews) Homestay
Free WiFi • Private bathroom • Non-smoking rooms
Best Price Match 
The Lyons' Lair Best Price Match
9.2 (26 Reviews) Apartment
The entire place is yours • 72 m² size • On-site parking
Chicago North Center • In Uptown · 2.0km to center
Best Price Match 
Luxury chicago suite Best Price Match
7.3 (51 Reviews) Apartment
The entire place is yours • 84 m² size • Free on-site parking
Chicago Lincoln Square • In Uptown · 4.1km to center
Best Price Match 
City Villa Sleeps 10-20 Free TV & Parking Best Price Match
9.3 (19 Reviews) Apartment
The entire place is yours • 232 m² size • Free on-site parking
Best Price Match 
Lincoln Park Living - Suite 2 Best Price Match
8.9 (20 Reviews) Holiday_home
The entire place is yours • 93 m² size • Free parking
Chicago Lincoln Park • In Uptown · 3.7km to center
Best Price Match 
The Roscoe Village Guesthouse Best Price Match
9.4 (15 Reviews) Apartment
The entire place is yours • 111 m² size • Free WiFi
Chicago North Center • In Uptown · 3.2km to center
Best Price Match 
Uptown Gem Best Price Match
9.3 (15 Reviews) Apartment
The entire place is yours • 42 m² size • Free parking
Best Price Match 
The Wrigleyville VIP-200 Steps from Wrigley Field Best Price Match
9.8 (12 Reviews) Apartment
The entire place is yours • 116 m² size • Kitchen
Best Price Match 
Penthouse Level, Stunning Wrigley Stay Best Price Match
8.9 (17 Reviews) Apartment
The entire place is yours • 110 m² size • Private parking
Best Price Match 
Game Day Getaway - 3BR in Vibrant Wrigleyville Best Price Match
9.3 (13 Reviews) Apartment
The entire place is yours • 148 m² size • Kitchen
Best Price Match 
1BR Fully Equipped & Central - Belmont rep Best Price Match
8.5 (16 Reviews) Apartment
The entire place is yours • 51 m² size • Pet friendly
Best Price Match 
Wrigleyville Friends Unit - 5bdrm Best Price Match
8.8 (14 Reviews) Apartment
The entire place is yours • 60 m² size • Pet friendly
Best Price Match 
1BR Modern Apt in the Heart of the City - Marshfield G Best Price Match
7.8 (21 Reviews) Apartment
The entire place is yours • 50 m² size • Pet friendly
Best Price Match 
Lakeview East Apartment Best Price Match
9.6 (9 Reviews) Apartment
The entire place is yours • 139 m² size • Free on-site parking
Best Price Match 
Wrigley Garden Unit Best Price Match
7.2 (22 Reviews) Apartment
The entire place is yours • 50 m² size • Pet friendly
Best Price Match 
Entire Apartment in heart of Lincoln Park & Lake Sea and beach Best Price Match
8.0 (15 Reviews) Apartment
The entire place is yours • 850 m² size • Free parking
Chicago Lincoln Park • In Uptown · 4.4km to center
Best Price Match 
Entire Apt in Heart of Chicago Best Price Match
9.7 (7 Reviews) Apartment
The entire place is yours • 88 m² size • Pet friendly
Best Price Match 
Indulging 2BR Apartment in Festive Boystown - Buckingham 1 Best Price Match
9.6 (7 Reviews) Apartment
The entire place is yours • 85 m² size • Pet friendly
Best Price Match About Uptown Vacation Rentals on NearbyHoliday
Looking for vacation rentals in Uptown? Compare top options in Chicago.
Find a Vacation Rental and Holiday Home in Uptown. Compare 74 family vacation homes, private villas, cottages, cabins, and condos in Uptown.
NearbyHoliday makes it easy to discover vacation rentals in Uptown that work well for families, groups, and longer stays when you want more room than a standard hotel setup.
Get More Room with NearbyHoliday.