If you’re travelling soon and wondering where to stay in Chicago 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. If you’re visiting for the first time, you can explore the city by participating in the various tours that take you around the city. Easily the city’s heartbeat, Streeterville encompasses the city’s famed Magnificent Mile, which features such famed buildings as the Wrigley Building and Tribune Tower. Within this neighbourhood, you’ll find a wonderful and diverse array of restaurants, and attractions such as the famed City Gallery and Millennium Park. Below, you can check out the best Vrbo vacation rentals in Streeterville, Chicago.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Blueground Streeterville Apartment (from USD 89)
If you’re looking to rent a two-bedroom apartment in Streeterville, Chicago, look no further. Enjoy this bright and airy apartment with cozy interiors during your next trip to Chicago. If the weather is pleasant, guests can take advantage of the on-site barbecue area and swimming pool. Health freaks can get their daily fix at the complex gym. The apartment has beautiful views of the Chicago skyline that guests can enjoy from the living room or while cooking in the fully equipped kitchen. The host boasts of luxury linens and mattresses assuring guests the utmost relaxation. The apartment is located only minutes away from The Loop, Navy Pier and the Michigan Avenue giving guests plenty to do without having to travel too far.
Nearby Vrbo Vacation Rentals
2. The Guild (from USD 428)
Enjoy this beautiful lakefront accommodation located in Chicago, near Streeterville. Located in downtown Chicago, this two-bedroom apartment is a comfortable haven located only a short walk away from the famous John Hancock Center, the Magnificent Mile and Michigan Avenue. Guests who want to experience lush greenery and picturesque views can visit Millennium Park and Grant Park.
The apartment itself boasts bright and spacious interiors with king-sized beds, a beautiful living room and a fully equipped kitchen. Guests can also access the building’s gym. The host takes pride in providing quality amenities such as bed linens, toiletries and free Wi-Fi. The property is wheelchair accessible as well.
3. Highrise apartment in Downtown, Chicago (from USD 254)
This Vrbo rental in downtown Chicago situated on the 50th floor boasts stunning views of the city from its floor-to-ceiling windows. This cosy yet spacious apartment comes with a modern fully equipped kitchen along with air conditioning. The host is gracious enough to provide guests with all basic amenities such as towels, bed linens and toiletries. The building has an outdoor pool, cooking area and gym that guests can access as they please.
As if the view wasn’t enough, this rental is also conveniently located near the glamorous North Michigan Avenue on one side and the eclectic and artsy River North District on the other. If travellers are looking for more adventure, it is also located close to motor boarding, sailing and fishing facilities near the lake. Guests can enjoy nearby fine dining restaurants and bars such as Tao, Quartino and Snickers.
4. Modern vacation home near Magnificent Mile (from USD 184)
Stay in the heart of Downtown Chicago at this modern vacation home, which is a part of the Best Western River North Hotel.. Enjoy a comfortable king bed and daily housekeeping. All linens, towels, and bathroom essentials are provided, so guests can travel light. The family-friendly property offers round the clock front desk service and security, an indoor pool, fitness center, and a rooftop deck with panoramic city views. On-site dining options are available at the hotels restaurant and bar. Other dining options in the area include restaurants such as Sushi-san, Fado Irish Pub and RPM Italian. A convenient and relaxing base for exploring the Windy City!
5. 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.
Top guest reviews
Amenities & Room:
Wonderful floor to ceiling windows facing the lake andStill cant get over the views from the roof and the condo itselfA pool game room and cable tvanywhere we wanted to be Plenty of space for 3 couples to coexist in the unitThe 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 )Cleanliness:
Everything was clean and as describedThe decor is beautiful - exactly as picturedVery good location with satisfied facilities and reasonable price3 bathrooms were great and the best was the viewsThe location couldn't be beat and the views of the lake and river were amazingHost:
He was so helpful and responsive to our inquiriesThe host (Juan) is amazing to work with he has outstanding communication skills and is very accomodatingthe next to final day being so strongThe manager Juan was very helpful in showing us the building and answering any questions we hadYou could control the temp within the unit and all appliances were in good working orderRead more reviewsLocation:
The location of this apartment was perfect Very close to all restaurants and shopping downtownThe location and views are incredibleThe location was perfect for us an easy walk to Navy Pier parksWe stayed at this property for 4 nights and enjoyed every minute of itGreat place with good views and close walks to stores
6. 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.
Top guest reviews
Amenities & Room:
Extra treat was being able to view the fireworks from the apartmentAll I can say the apartment was even better than the pictures showI was in town with a colleague for a conferenceThe property is nice and clean with a gorgous view of lake and navy pierWe really enjoyed our stay - loved having both the river view and the lake viewCleanliness:
I hope to return soon CheersJuan made our check in very easy and the apartment was clean and the beds super comfortableHost:
Great first-time experience with Vrbo Wonderful property with nice amenitiesThe property manager was super friendly helpful and very accommodatingThey were prompt in answering any questions we hadLocation accommodations and communication were greatbright quiet lovely views Worked out well for our family that included a young childRead more reviewsLocation:
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 comfortableA great place to stay in downtown ChicagoRight in the heart of downtown Chicago a short walk to the Navy PierThere were plenty of grocery stores restaurants and coffee shops within a block or two; same for public transitAmazing views from every window Easy to walk to Michigan avenue and other spots throughout Great location for a family trip
7. 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.
Chicago, IL, US
8. 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 Wi-Fi, 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.
Chicago, IL, US
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 which means once you’ve visited the 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. Guests can have a blast in the vibrant downtown Chicago which offers tourists plenty of things to do.
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.
Frequently asked questions about Vrbo vacation rentals in Streeterville, Chicago
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