4 Best Vrbo Vacation Rentals In Streeterville, Chicago, Illinois


If you’re going to Chicago–and it’s recommended that you do to experience the city’s marvellous culture, nightlife, and dining opportunities–then you couldn’t make a better choice than to base yourself in and around the Streeterville neighbourhood. Easily the city’s heartbeat, Streeterville encompasses the city’s famed Magnificent Mile, which is the commercial heart of the city and features such famed buildings as the Wrigley Building and Tribune Tower. Within this neighbourhood you’ll find a wonderful and diverse array of restaurants, along with attractions such as the famed City Gallery and Millennium Park. Below, you can check out the best Vrbo accommodations in Streeterville, Chicago and pick your base for a holiday you’ll never forget.

1. Spacious three-bedroom loft with spa facilities (from USD 778)

Guests in this accommodation will be delighted with what it has to offer–thanks to its loft set-up you’ll have superb views of the city, while you’re close to the excellent rooftop pool that’s on offer to residents in the building. The room offers floor-to-ceiling windows, giving plenty of natural light and staggering views of the city, while a gourmet kitchen will delight any keen cooks in your party. Six guests can fit across three bedrooms, and your stay will be highly comfortable–among the many luxurious touches is a communal hot tub.

3B/3BA Luxury Sky Loft | Panoramic Views, Indoor Pool & Gym
37 reviews  Wifi Available
Apartment 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Wonderful floor to ceiling windows facing the lake and
Still cant get over the views from the roof and the condo itself
A pool game room and cable tv
anywhere we wanted to be Plenty of space for 3 couples to coexist in the unit
The apartment is on a high floor with views out in two directions - city and lake (the master is in the corner with glass walls all around - stunning )
Everything was clean and as described
The decor is beautiful - exactly as pictured
Very good location with satisfied facilities and reasonable price
3 bathrooms were great and the best was the views
The location couldn't be beat and the views of the lake and river were amazing
He was so helpful and responsive to our inquiries
The host (Juan) is amazing to work with he has outstanding communication skills and is very accomodating
the next to final day being so strong
The manager Juan was very helpful in showing us the building and answering any questions we had
You could control the temp within the unit and all appliances were in good working order
The location of this apartment was perfect Very close to all restaurants and shopping downtown
The location and views are incredible
The location was perfect for us an easy walk to Navy Pier parks
We stayed at this property for 4 nights and enjoyed every minute of it
Great place with good views and close walks to stores
Read more reviews

2. Seven-person apartment with family-friendly facilities (from USD 823)

Any group travelling with young children will be delighted by this family-friendly accommodation. Three bedrooms and three bathrooms ensure that everyone can be comfortable staying here, with the bedrooms are stocked with luxury Egyptian cotton bedding. One thing that particularly stands out is the attention that has been paid to ensuring families with babies and young kids are taken care of. At this accommodation you’ll have access to everything from cribs, to books, to a diaper genie should you need it. Nearby, you’ll have plenty of shopping options, along with dining at some of the city’s best restaurants and the fantastic Navy Pier complex for entertainment.

3B/3BA Massive Luxury Apartment | Views, Indoor Pool & Gym
49 reviews  Wifi Available
Apartment 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Extra treat was being able to view the fireworks from the apartment
All I can say the apartment was even better than the pictures show
I was in town with a colleague for a conference
The property is nice and clean with a gorgous view of lake and navy pier
We really enjoyed our stay - loved having both the river view and the lake view
I hope to return soon Cheers
Juan made our check in very easy and the apartment was clean and the beds super comfortable
Great first-time experience with Vrbo Wonderful property with nice amenities
The property manager was super friendly helpful and very accommodating
They were prompt in answering any questions we had
Location accommodations and communication were great
bright quiet lovely views Worked out well for our family that included a young child
The apartment is in a wonderful location just minutes form the Navy Pier walking distance to great restaurants and shops and well suited for 2 families to spread out and be comfortable
A great place to stay in downtown Chicago
Right in the heart of downtown Chicago a short walk to the Navy Pier
There were plenty of grocery stores restaurants and coffee shops within a block or two; same for public transit
Amazing views from every window Easy to walk to Michigan avenue and other spots throughout Great location for a family trip
Read more reviews

3. Art Deco accommodation for two on the North Side

The clean lines and bold colours of the Art Deco style are very much in evidence at the Cambria and booking into your accommodation here will ensure that you stay in comfort and are looked after well. Each room offers access to concierge service, wireless internet and a 24/7 fitness centre. An onsite cafe-bar offers dining and drinking options, including barista-style coffee, and each room comes with a 42-inch (106.68-cm) TV providing cable channels for your entertainment.

The Chicago Hotel Collection - Magnificent Mile
Chicago, IL, US
2 Guests 0 Bedrooms 0 Bathrooms

4. Four-person studio with plenty of extras

An unbeatable view of the Chicago skyline awaits you as a guest at the Embassy Suites, and this studio-style apartment delivers much more on top of that. With free WiFi, a kitchenette, and one king-sized bed among other amenities, the suite makes full use of its 425 sq. ft. (39 sq. m.) of floor space. Throw in an additional double sofa-bed, free toiletries, and a complimentary daily newspaper, as well as air conditioning and daily housekeeping, and you have an apartment that delivers more than you could imagine.

Embassy Suites Chicago Downtown Magnificent Mile
Chicago, IL, US
4 Guests 1 Bedroom 1 Bathroom

It's not just the Mile that's magnificent--see Streeterville at its best

Chicago may not have the same glitzy reputation that New York or Los Angeles on the coasts can boast but for many people that’s part of the attraction. There is a soul to this city that means once you’ve visited a first time, you’ll be keen to keep coming back. Streeterville is a major component of that soul, being home to most of Chicago’s iconic architecture, having excellent food from the streets and the restaurants, and being in close proximity to attractions such as Navy Pier. As these accommodations demonstrate, while other cities may come out ahead on glamour and glitter, there is no shortage of luxury and comfort to be found in Streeterville–everything about this place will make you feel just fine about your time in Chicago.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Antonia Kelly is a freelance writer based in Leicester, UK and she enjoys European travel as well as road trips closer to home. Her favourite domestic destinations include Snowdonia and the Brecon...Read more

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