Cool Downtown Chicago VRBO Rentals
If you are traveling to Chicago one of the biggest decisions to make is ‘where to stay’? I’m pretty partial to a luxury hotel, but if traveling with a large group of family or friends then getting a short-term rental, aka VRBO, can be a pretty fun way to enjoy the city.
Short-term rentals have become very popular in recent years, with sites like Airbnb and VRBO dominating the scene. The two sites have a few differences but are mostly similar in that they are phone-app based, feature a large selection of accommodations, and offer multiple filters to hone in on exactly what you are looking for. While Airbnb technically has more inventory, because VRBO only rents entire spaces (no single rooms like Airbnb) I prefer to start my search there. VRBO also lets you filter on some advanced features, like private pool, that Airbnb doesn’t.
One, if not the, most important things to look at when deciding where to stay is location, location, location. Especially in a city like Chicago that has a wide range of neighborhoods (downtown or trendy?) and features (by the water or the train?) you don’t want to be disappointed by where you are staying. Luckily, I’ve done the research for you, and here are some awesome VRBO options in Chicago.
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Sleeps 8
Single Family Mansion
Want to stay in what I assume is a multi-million dollar home in Chicago? This is it. This beautiful single-family home with a garage is in the most prestigious part of the city. 4 bedrooms, 5 bathrooms so although it will cost you, would be a gorgeous place to stay for a multi-family vacation or a group of friends. I mean there’s a legit wood-burning fireplace in the bathroom. I’m pretty sure this bathroom is bigger than the blue banana. There is a private outdoor space although since it’s a single-family home surrounded by high rises it doesn’t really have that much privacy.
Sleeps 8
Penthouses Don’t Come on the First Floor
Pricy? Yes. But these are million-dollar views in this penthouse we’re talking about. And a huge private outdoor space. The living room takes up two full stories so with the wall of glass you can see quintessential Chicago landmarks… the Handcock, the shops at 900 N Michigan Ave, Lake Michigan. It’s a stunning apartment. The unit also has access to the outdoor pool, which isn’t super common in the city, if you are here in the summer and a pool is more your vibe than the beach. Although don’t discount Chicago beaches
Sleeps 5
Great for Shopping
This apartment feels like a boutique hotel room. With floor-to-ceiling windows and a private balcony, this is a sweet 2 bedroom. Situated between Oak Street and Magnificent Mile, there is an abundance of shopping options to choose from.
Sleeps 4
Entertainer’s Delight
This single-family home is technically in Old Town, which is north of downtown, but it’s close to Second City, 3 Arts Club Cafe, and a ton to do. Not only is this not your typical high-rise vibe, but the chandelier in the dining room also screams glamour. The owners will connect you with a private chef or baker in case you also want to have a dinner party or celebrate a birthday. How cool is that?
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River Views
With an outdoor pool, this apartment is in the heart of the city. Here you can take advantage of both the Chicago River and architecturally rich skyline views. Since it’s right by the Merchandise Mart you may hear the train, but on the bright side you’ll be very close to the world-class el system.
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Views for Days
This penthouse features awesome views of Lake Michigan, the Chicago River, and Navy Pier. The inside is nicely furnished but it’s all about the views and the location. And reasonably priced for bedrooms in the city, it would be hard to find that at a hotel.
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City Living
This 2 bedroom apartment may be basic but it has everything you need to feel like you are living the city life. Floor to ceiling windows, a private balcony, and an outdoor pool in the center of the city.
Coming to Chicago? Check out these posts before you come.
- The Best of Chicago (what to do, where to go, what to eat)
- 3 Day Chicago Itinerary for the Spring & Summer
- 23 Cool Hotels in Chicago
- Fall and Winter 3 Day Chicago Itinerary
Before you travel, make sure your toiletry bag is stacked!
DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.
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