Gather your favorite people at 'The Winfrey,' our exclusive offering of two luxury apartments, perfect for your group's special Chicago gathering.
Our commitment to a pristine stay is clear, with a perfect 100% 5-star cleanliness rating from all of our guests since 2024.
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.
- Spacious living areas + full kitchens in both units
- 10 min to Chicago Theater; 13 min to Millennium Park
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:
- Parking $50/night (spots are limited, so ask when you book to check availability)
- Check-in 4 pm (same-day 6 pm), check-out 11 am
- $2000 refundable deposit via credit card; gov’t ID + standard background check for all adults
- No pets allowed
Check your dates now—group-friendly rentals fill up quickly!
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Cloud9 House Rules 1. Trust and Safety: Prior to accepting a reservation, we conduct thorough screening of every guest to ensure that they comply w...
Important information
You need to know
Property Registration Number R22000085442
Property # 4218044vb
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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Chicago
Located on the waterfront, this apartment is in Downtown Chicago, a neighbourhood in Chicago. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Field Museum of Natural History and Lincoln Park Zoo. Check out an event or a game at Soldier Field, and consider making time for Griffin Museum of Science and Industry, a top attraction not to be missed. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with cycling and rock climbing.
Does Two 2BRs Near Millennium Park, Ideal for Groups have a pool?
Yes, this property has a pool.
How much does it cost to stay at Two 2BRs Near Millennium Park, Ideal for Groups?
As of 7 July 2026, prices found for a 1-night stay for 2 adults at Two 2BRs Near Millennium Park, Ideal for Groups on 15 Nov 2026 start from AU$1,910, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Two 2BRs Near Millennium Park, Ideal for Groups pet-friendly?
No, only service animals are welcome at the property.
How much is parking at Two 2BRs Near Millennium Park, Ideal for Groups?
On-site parking is available at the property.
What time is check-in at Two 2BRs Near Millennium Park, Ideal for Groups?
Check-in begins at 4:00 PM.
What time is check-out at Two 2BRs Near Millennium Park, Ideal for Groups?
Checkout is at 11:00 AM.
Where is Two 2BRs Near Millennium Park, Ideal for Groups located?
Located in Downtown Chicago, this apartment building is within a 10-minute walk of Daley Plaza, Millennium Park and Michigan Avenue. Chicago Riverwalk and Willis Tower are also within 15 minutes. Monroe Station (Blue Line) and Washington-Wells Station are within a 5-minute walk.
Reviews
9.2
Wonderful
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We loved our stay and were very pleased with cleanliness, ease of check in, and communication throughout. Had a 2 and 5 year old and the roof top pool was nice to kill a couple hours.
Terry M.
Stayed 3 nights in Jun 2025
Response from VrboOwner on 11 Aug 2025
We are thrilled to hear that your stay at Cloud9 was enjoyable and that our cleanliness, seamless check-in, and attentive communication exceeded your expectations. It's wonderful that your little ones enjoyed the rooftop pool, making delightful memories with you. We look forward to welcoming your family back for more cherished moments.
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.
Tom L.
Stayed 3 nights in Apr 2025
Response from VrboOwner on 11 Aug 2025
We are grateful for your kind words about our immaculate property and its prime location within the Chicago Loop. It's delightful to know that our surroundings offered you such convenient access to the city's vibrant culture. We look forward to welcoming you back for your next adventure at Cloud9.
The good,bad,and ugly-Good-the property was in an excellent location, it was very clean and appointed, there were lots of spaces in the building to enjoy, the communication and response time from Cloud9 was excellent prior to the trip. The Bad- we had prearranged for pack and plays long before our arrival. They were not there and Cloud9 could not resolve the issue prior to nighttime (with 2 three yr olds with no place to sleep) so we solved it by going to Target and purchasing the equipment. They did readily reimburse us but this was not part of our plans for our son’s wedding weekend. The Ugly- the building has extremely noisy trash pick up in the middle of the night-metal bins over concrete. This happened 2 of our 4 nights. This is in no way a problem with Cloud9 or VRBO but I did not see it mentioned in any of the reviews prior to booking. All in all, it was a wonderful celebration weekend.