Two Units: Seamless Stay, Downtown Convenience | Apartment in Chicago

10.0 (3 Reviews) |   Pet Friendly   4 Bedrooms  4 Bathrooms  10 Guests
Downtown Chicago Apartment | Two Units: Seamless Stay, Downtown Convenience

4 Bedroom Apartment in Downtown Chicago, Chicago

Summary:
Your perfect spot for large groups in downtown Chicago! 'The Winfrey' offers two 2BR apartments in the same building, providing resort-style amenities for an unforgettable experience in the heart of the city near iconic attractions.
The Space:
We manually verify all reservations, as our units are rented individually and the calendar may not reflect real-time status. In the rare event of a scheduling conflict, we guarantee to provide you with excellent alternative options. Your booking is considered final only upon receiving our confirmation message.
This collection includes two distinct 2BR apartments.
Each unit features a luxurious queen bedroom with a TV, walking closet, and ensuite bathroom. The second bedroom includes a comfortable queen bed, closet, and a full hall bathroom.
Each apartment offers a full kitchen equipped with top brands and a spacious living room with a Sonos sound system.
A Pack & Play is available upon request, and two rollaway beds are included in the units for extra guests.
Guest Access:
The building also offers exceptional amenities, including:
- Sundeck
- BBQ/Picnic Area
- Conference Room
- Basketball Court
- Game Room
- Movie Theater
- Outdoor Pool
- Rooftop Lounge
- Media Room
- 24/7 Fitness Center
- Bocce Ball Court
- Poker Lounge
Please note that the availability of some of these amenities may vary seasonally and could potentially incur additional fees.
The Neighborhood:
Nestled in the premier location adjacent to Millennium Park, The Loop offers the ultimate rental living experience. With Lakefront paths, Riverwalk, Grant Park, Michigan Avenue, theaters, museums, restaurants, shopping, and much more at your doorstep, it's a true epitome of upscale urban living. Here, you can enjoy a lifestyle where theater, entertainment, recreation, and career opportunities are all just steps away.
Getting Around:
What’s Nearby:
The Art Institute – 13-min walk
Millennium Park – 13-min walk
Skydeck Chicago - Willis Tower – 10-min walk
Target – 3-min walk
Walgreens – 3-min walk
Riverwalk – 10-min walk
Chicago theater – 12-min walk
Nordstrom Rack – 8-min walk
You’re in the financial district, with easy access to nearby banks
Other Things to Note:
- For the safety of all our guests, we handle a $2000 security deposit via credit card and a simple background check, requiring valid ID from all adults. Please review our house rules before booking.
- Parking Policy: Parking is $50 per night. Spots are limited, so ask when you book to check availability!
- Pet Policy: Pets are welcome with prior approval, subject to a 35-pound weight limit and breed restrictions. A fee of $50 per night applies. For more details, please contact us directly. Any damages caused by pets will be billed at the end of the stay.
- Our standard time for check-in is 4:00 PM. For reservations made on the same day of arrival, the earliest possible check-in time is 6:00 PM.
Traveling with a larger group? Exploring other neighborhoods? We have multiple apartments across Chicago—message us for recommendations!

Two Units: Seamless Stay, Downtown Convenience is located in Downtown Chicago. Two Units: Seamless Stay, Downtown Convenience provides accommodation, featuring Barbecue/Outdoor Cooking, Air Conditioner, Accessibility, among other amenities. This Apartment features Barbecue/Outdoor Cooking, Air Conditioner, Accessibility, to make your stay a comfortable one.

Two Units: Seamless Stay, Downtown Convenience has 4 Bedrooms , 4 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have rated it 2, and VRBO labeled it a top-rated Apartment because of the excellent services rendered by the owner or manager of this Apartment, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Apartment has a friendly neighborhood, and the Downtown Chicago has interesting places to visit. If you want to learn more about the Apartment in Downtown Chicago, such as places to visit and things to do nearby, you can check below to learn more.

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Chicago, 60603, United States

Amenities

Air Conditioner
Pet Friendly
Pool
TV
Wheelchair Accessible
Accessibility
Security/Safety
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Heating
  • Air conditioning
Bathrooms
  • Shower
  • Towels provided
  • Hair dryer
  • 4 bathrooms
Bedroom
  • Bed sheets provided
  • 4 bedrooms
Kitchen
  • Oven
  • Microwave
  • Cookware/dishes/utensils
  • Coffee/tea maker
  • Dishwasher
  • Refrigerator
  • Stovetop
Laundry
  • Laundry facilities
  • Washing machine and dryer
Pet Friendly
  • Pet friendly
Accessibility
  • Smoke-free property
  • Elevator
Activities
  • Rock climbing nearby
  • Casino nearby
  • Fitness center
  • Cycling nearby
Entertainment
  • Stereo
  • TV
General
  • On the river
  • Near a zoo
  • In the city center
  • On the waterfront
  • Office
Guest Services
  • Travel crib
  • Iron/ironing board
Internet
  • WiFi available
Outdoors
  • Barbecue grill
Security/Safety
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • First aid kit
  • Fire extinguisher
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
Spa
  • Shared/communal pool

Policies

Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Note from host: charge may apply pets allowed service animals are welcome, and are exempt from fees
Smoking Policy
Smoking is not permitted
Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited property registration number r22000085442 safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property accepts cash this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
License number: R22000085442

Reviews

Tom L.
Apr 28, 2025 09:58:42 PM
Review Score:   10
Summary: The property was meticulous, convenient and secure. Centrally located within the Chicago loop, Chicago art museaum, arhitectural tour and Buddy Guy's Blues club are all within alking distance. Already planning a trip for next year.
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FAQ's

Is this Downtown Chicago apartment pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Downtown Chicago apartment have a swimming pool?

Yes, this Downtown Chicago apartment has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Downtown Chicago apartment?

Best-rates for the Downtown Chicago apartment starts from $1,405 per night with includes Wellness Facilities, Entertainment, Kitchen, Pool, Bedding/Linens, Child Friendly, Internet, Pet Friendly, TV, Wheelchair Accessible, Fireplace/Heating, Barbecue/Outdoor Cooking, Air Conditioner, Accessibility, Laundry, Security/Safety with all other facilities. RBO matches every traveller with their perfect accommodation, whether you are travelling with a group, friends, family, or pets.

Is Downtown Chicago apartment a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this apartment 2 stars or guests have recommended them suitable for families. As reported by the owner or manager, the apartment has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Downtown Chicago apartment wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Downtown Chicago apartment is wheelchair accessible. Likewise, there is an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Downtown Chicago apartment?

Based on the information reported by the owner or manager, the Downtown Chicago apartment indicates 1 day stay policy at this apartment. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Downtown Chicago apartment?

Based on the information reported by the owner or manager, details for the cancellation policy for the Downtown Chicago apartment are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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