Budget-Friendly Stay and Free Coffee | Downtown
Budget-Friendly Stay and Free Coffee | Downtown
Budget-Friendly Stay and Free Coffee | Downtown
Budget-Friendly Stay and Free Coffee | Downtown
Budget-Friendly Stay and Free Coffee | Downtown

Budget-Friendly Stay and Free Coffee | Downtown

1 bedroom·2 baths
Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Traveler’s Favorite: Private Room Near Attractions
Traveler’s Favorite: Private Room Near Attractions
Traveler’s Favorite: Private Room Near Attractions
Traveler’s Favorite: Private Room Near Attractions
Traveler’s Favorite: Private Room Near Attractions

Traveler’s Favorite: Private Room Near Attractions

1 bedroom·2 baths
Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

TOP PICK: Solo/Group, Private Rooms, Free Coffee!
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
TOP PICK: Solo/Group, Private Rooms, Free Coffee!

TOP PICK: Solo/Group, Private Rooms, Free Coffee!

1 bedroom·2 baths
Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Secure, Private, Free Wi-Fi and Coffee, Accessible
Secure, Private, Free Wi-Fi and Coffee, Accessible
Secure, Private, Free Wi-Fi and Coffee, Accessible
Secure, Private, Free Wi-Fi and Coffee, Accessible
Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible

1 bedroom·2 baths
Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!

All Ease Private Stay |Traveler's Top Fave!!

1 bedroom·2 baths
Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

Chicago Lakefront · Fire Pit Patio · Beach Across image 1
Chicago Lakefront · Fire Pit Patio · Beach Across image 2
To the right: two plush couches and a large window. Opposite you: a mounted TV and a table with four chairs. To the right of the table is a corner desk with a lamp. A large rug anchors the center floor. Simple, clear, and easy to navigate.
Chicago Lakefront · Fire Pit Patio · Beach Across image 4
Chicago Lakefront · Fire Pit Patio · Beach Across image 5

Chicago Lakefront · Fire Pit Patio · Beach Across

1 bedroom·1 bath
Chicago • Illinois
5(1 review)

$467.00 USD $373.60 USD total for 3 nights

Nov 8 – 11, 2026

Exterior
Living area
Living area
Interior
Room

Chic 2-bedroom apartment in beautiful Chicago. 30+ Day Stays Only

2 bedrooms·2 baths
Chicago • Illinois

$4,170.00 USD total for 30 nights

Nov 3 – Dec 3, 2026

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown
Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown
Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown
Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown
Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

3 bedrooms·2 baths
Chicago • Illinois

$812.00 USD total for 3 nights

Nov 3 – 6, 2026

balcony
Master Bedroom Second Floor
Family Room First Floor open to Loft Second Floor two story family room with skylights
Master Bedroom Second Floor
Kitchen First Floor

Beautiful spacious gem Oasis Manor 6 BR 4 1/2 BA

6 bedrooms·4 baths
East Dundee • Illinois
5(9 reviews)

$2,766.75 USD total for 3 nights

Nov 3 – 6, 2026

Charming ranch home with vibrant fall views and glowing sunset curb appeal
*King bed *Outdoor Living *Sought-After Area
*King bed *Outdoor Living *Sought-After Area
Charming backyard lounge with cozy deck seating and private garden vibe
Cozy boho lounge with greenery, armchairs, and warm natural accents

*King bed *Outdoor Living *Sought-After Area

3 bedrooms·1½ baths
Northbrook • Illinois
5(135 reviews)

$1,491.00 USD total for 3 nights

Nov 19 – 22, 2026

Large Cozy 3BR near UChicago Medical Midway Museum
Living Room
Main bedroom from desk area
Second bedroom -- a headboard has been added (didn't get a picture of that yet).
Third bedroom, desk and closet

Large Cozy 3BR near UChicago Medical Midway Museum

3 bedrooms·1 bath
Chicago • Illinois
5(8 reviews)
$349/ night(excl. fees & taxes)
Hyde Park 2BR UChicago Medical Museums 20% OFF
Main Bedroom
Hyde Park 2BR UChicago Medical Museums 20% OFF
Hyde Park 2BR UChicago Medical Museums 20% OFF
Quick view of upstairs "half kitchen," middle of tile restoral. NOTE there is a microwave and induction burner, NO STOVE.

Hyde Park 2BR UChicago Medical Museums 20% OFF

2 bedrooms·1 bath
Chicago • Illinois
5(4 reviews)
$233/ night(excl. fees & taxes)
Step into serenity at our welcoming retreat. Follow detailed check-in directions to unlock the smart lock for secure access. Relax in the cozy living room with a 30" Smart TV and a collection of board games. Outside, unwind in the serene backyard.
Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.
Unwind in our inviting sanctuary. Seamless check-in with detailed instructions and a smart lock. Cozy up in the relaxing living room, equipped with a 30" Smart TV and a selection of board games. Step outside to a tranquil backyard with a pergola.
Step into tranquility with seamless check-in and a smart lock. Explore local treasures with our custom guidebook. Outside, unwind in the serene backyard oasis, complete with a pergola, fire-pit, outdoor gas grill, and picnic table dining.
Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.

Artistic Stay near Hyde Park: 2 Living, Courtyard

3 bedrooms·2½ baths
Chicago • Illinois
4.9(106 reviews)

$817.00 USD total for 3 nights

Nov 3 – 6, 2026

The Euclid House — 6BR Near UChicago & Hospitals
The Euclid House — 6BR Near UChicago & Hospitals
The Euclid House — 6BR Near UChicago & Hospitals
The Euclid House — 6BR Near UChicago & Hospitals
The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

6 bedrooms·3 baths
Chicago • Illinois

$1,100.00 USD total for 3 nights

Nov 3 – 6, 2026

What a view from my 13th floor!
Stately building entrance
Gallery Hallway looking towards Living Room
Spacious living room
My view of Jackson Harbor and partial Chicago skyline.

Art Collector's Pied-à-terre

2 bedrooms·2 baths
Chicago • Illinois
4.84(247 reviews)

$2,980.00 USD total for 32 nights

Nov 5 – Dec 7, 2026

Waterfront Cottage/sauna/kayaks/firepit/dock image 1
Waterfront Cottage/sauna/kayaks/firepit/dock image 2
Waterfront Cottage/sauna/kayaks/firepit/dock image 3
Waterfront Cottage/sauna/kayaks/firepit/dock image 4
Waterfront Cottage/sauna/kayaks/firepit/dock image 5

Waterfront Cottage/sauna/kayaks/firepit/dock

1 bedroom·1 bath
Fox River Grove • Illinois
4.88(40 reviews)

$765.00 USD total for 3 nights

Nov 3 – 6, 2026

6 bedroom! Pool Table, Gaming Area, Firepit & More image 1
6 bedroom! Pool Table, Gaming Area, Firepit & More image 2
6 bedroom! Pool Table, Gaming Area, Firepit & More image 3
6 bedroom! Pool Table, Gaming Area, Firepit & More image 4
6 bedroom! Pool Table, Gaming Area, Firepit & More image 5

6 bedroom! Pool Table, Gaming Area, Firepit & More

6 bedrooms·3 baths
Joliet • Illinois
4.92(24 reviews)

$2,390.00 USD total for 3 nights

Nov 3 – 6, 2026

Wind down under the cozy lighting at the end of your day. Relax in the hot tub or gather around the fire table.
Regulation size pickleball court with Sport Court surface is only shared with guests who book the Guest Quarters.
The LED lights on the corn hole boards can make playing in the evening more adventurous.
Warning! Playing these games may cause competitive natures to rise and may lead to tears and belly aches from too much laughing.
View down from the top of the stairs.Caution! Top step is more shallow than other steps.

Deer Run Log Cabin

3 bedrooms·2 baths
Yorkville • Illinois

$2,112.80 USD $2,007.17 USD total for 3 nights

Nov 3 – 6, 2026

Private deck with fire table, seating, BBQ grill, hot tub, and glowing café lights—perfect for relaxing nights outdoors.
The onsite pickleball court has a Sport Court surface and is shared with the guests in the Cabin. Deer frequently pass by the court.
Relax by the fire table in the gazebo.
The corn hole boards have LED lighting that make playing at dusk more exciting.
Shared Space: Bond and laugh over some board games.

Deer Run Guest Quarters

1 bedroom·1 bath
Yorkville • Illinois
5(1 review)

$1,066.65 USD $1,024.00 USD total for 3 nights

Nov 4 – 7, 2026

Regulation size pickleball court with Sport Court surface on site!
Unwind on the deck under the cafe lights or around the fire pit.
There is plenty of comfortable seating so everyone in your group can have a seat without crowding each other. There are even throw blankets and pillows for additional comfort.
Relax in the 7-person hot tub under the cafe lights at night.
Everyone in your group can sit around the table together as it seats up to 12 people. There are also 2 additional seats at the kitchen island..

Deer Run Lodge

4 bedrooms·3 baths
Yorkville • Illinois
5(1 review)

$3,339.01 USD $2,838.16 USD total for 3 nights

Nov 4 – 7, 2026

Charming Getaway in Homewood Near Chicago
Spacious Living Room, opened up to the Dining Room
Modern Fully Stocked Kitchen
Upstairs Living Room, off the Master Bedroom
Private workspace

Charming Getaway in Homewood Near Chicago

3 bedrooms·1½ baths
Homewood • Illinois

$706.00 USD total for 3 nights

Nov 3 – 6, 2026