
North Side Vacation Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for North Side vacation rentals

1. Chic Urban Retreat Near Wrigley Field w/Parking
Chic Urban Retreat Near Wrigley Field w/Parking
2. Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
3. 5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10 - Pet Friendly
5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10 - Pet Friendly
4. Elite 2BR Art Deco sanctuary. High style.
Elite 2BR Art Deco sanctuary. High style.
5. Great Area Logan Square Apt Games Pets - Sleeps 5
Great Area Logan Square Apt Games Pets - Sleeps 5
6. Cozy 3BR Gem in North Center
Cozy 3BR Gem in North Center
7. Wrigley Field MVP Suite 1 Bedroom Apartment
Wrigley Field MVP Suite 1 Bedroom Apartment
8. Minutes to Wrigley - Games - Patio - Sleeps 12
Minutes to Wrigley - Games - Patio - Sleeps 12Find vacation rentals that suit your style
Top North Side Hotel Reviews

The Willows Hotel
Find out more about North Side
Everything you need to know about North Side vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the North Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect North Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
North Side vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in North Side. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Side vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of North Side vacation rentals we have selected for you start as low as CA $272 per night. Entering your travel dates in the search wizard you might find even better deals!
How to find incredible deals on North Side rentals
At Expedia, we put the best North Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top North Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream North Side vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around North Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Explore a world of travel with Expedia
- Hotels with a Pool in Chicago
- Hotels near O'Hare Intl.
- Hotels near Soldier Field
- Boutique Hotels in Chicago
- Wrigleyville Hotels
- Hotels near United Center
- Downtown Chicago Hotels
- Hotels with Kitchenettes in Chicago
- Pet-Friendly Hotels in Chicago
- Hotels near Art Institute of Chicago
- Hotels near McCormick Place
- West Loop Hotels
- River North Hotels
- Hotels with Free Parking in Chicago
- The Loop Hotels
- Gold Coast Hotels
- All Inclusive Resorts and in Chicago
- Marriott Hotels & Resorts in Chicago
- Wicker Park Hotels
- Hostels in Chicago
- Magnificent Mile Hotels
- Lincoln Park Hotels
- Cheap Hotels in Chicago
- Motels in Chicago
- Luxury Hotels in Downtown Chicago
- Hotels near Michigan Avenue
- Hotels near Cloud Gate
- 5 Star Hotels in Chicago
- Hotels near Millennium Park
- Fulton Market Hotels
- Hotels near Navy Pier
- Chicago Hotels
- Hotels near Chicago Union Station
- Hotels near Chicago Riverwalk
- Cheap Hotels in Downtown Chicago
- Hotels near Wrigley Field
- Family Hotels in Chicago
- Hotels near Grant Park
- Hotels with Free Breakfast in Chicago
- Hotels with Free Airport Shuttle in Chicago
- Flights from Toronto (YYZ) to Chicago (MDW)
- Flights from Victoria (YYJ) to Chicago (ORD)
- Flights from Saskatoon (YXE) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Kelowna (YLW) to Chicago (ORD)
- Flights from O'Hare Intl.
- Flights from New York (LGA) to Chicago (ORD)
- Flights to Chicago
- Flights from Calgary (YYC) to Chicago (ORD)
- Flights from Toronto (YTZ) to Chicago (MDW)
- Flights from Halifax (YHZ) to Chicago (ORD)
- Flights from Buffalo (BUF) to Chicago (ORD)
- Flights from Montreal (YUL) to Chicago (ORD)
- Flights from Chicago
- Flights from Edmonton (YEG) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from Kitchener (YKF) to Chicago (ORD)
- Flights from Hamilton (YHM) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Midway Intl.
- Flights from Waterloo (ALO) to Chicago (ORD)
- Flights from London (YXU) to Chicago (ORD)
- Flights from Ottawa (YOW) to Chicago (ORD)
- Flights from Winnipeg (YWG) to Chicago (ORD)
- Flights from Regina (YQR) to Chicago (ORD)
- Flights from Minneapolis (MSP) to Chicago (ORD)
- Flights from Windsor (YQG) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Art Institute of Chicago
- Navy Pier
- Visit West Loop
- Lincoln Park Zoo
- Visit Downtown Chicago
- Visit The Loop
- Visit Magnificent Mile
- Grant Park
- Wrigley Field
- Visit Lincoln Park
- Water Tower Place
- All inclusive Vacation Packages Chicago
- Chicago Vacations
- Visit Chicago
- Willis Tower
- Millennium Park
- Chicago Riverwalk
- Golf Vacations
- Downtown Chicago Vacations
















































































