Where to stay around Oakland, Chicago?

Our 2019 property listings offer a large selection of 25 vacation rentals near Oakland. From 10 Houses to 10 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oakland for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Oakland?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Oakland:

  • Lakeview: 301 vacation rentals
  • Chicago Loop: 700 vacation rentals
  • Streeterville: 201 vacation rentals
  • Old Town: 236 vacation rentals
  • Wrigleyville: 328 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

Can I rent Houses in Oakland?

Yes, of course. VRBO has 10 Houses in Oakland. Our other popular types of vacation rentals in Oakland include:

  • Condos/Apartments: 10 rentals available
  • Studios: 8 rentals available
  • Townhouses: 3 rentals available

Can I find a vacation rental with internet/wifi in Oakland?

Yes, you can select your prefered vacation rental with internet/wifi among our 24 vacation rentals with internet/wifi available in Oakland. Please use our search bar to access the selection of vacation rentals available.

    Explore the beachside setting in Oakland

    The beaches and lake provide a pleasant backdrop to your vacation home in Oakland. Well-liked for its restaurants, skyscrapers and shopping, this city is both cosmopolitan and scenic. McCormick Place and Willis Tower are just a couple of the must-sees in the area. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

    Sightseeing in and around Oakland

    Are you searching for top things to see and do while you're in town? Venture out of your vacation home and experience everything that makes Oakland a fun spot to vacation. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

    • Skydeck Ledge (4.1 mi / 6.7 km)
    • Adler Planetarium and Astronomy Museum (2.9 mi / 4.7 km)
    • John G. Shedd Aquarium (3 mi / 4.8 km)
    • Navy Pier (4.7 mi / 7.6 km)
    • Lincoln Park Zoo (6.8 mi / 11 km)
    • Brookfield Zoo (11.9 mi / 19.2 km)

    Exploring the natural landscape of Oakland

    Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Oakland. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

    • Millennium Park (4.2 mi / 6.7 km)
    • Grant Park (3.5 mi / 5.7 km)
    • Lincoln Park (8.9 mi / 14.4 km)
    • Burnham Park (0.4 mi / 0.6 km)
    • Lake Meadows Park (1 mi / 1.6 km)
    • Lakefront Trail (1.2 mi / 2 km)