Holiday houses in Montrose Beach

13 mins DT | 4 mins Lake | Artistic Loft Rooftop

*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart TV, and a dedicated workstation, ideal for traveling professionals or remote workers. Unwind in comfort with an in-unit washer/dryer, dishwasher, and access to a rooftop area for breathtaking city views. Stay in shape with a fitness center. Steps away from Montrose Beach, Aragon Ballroom, and Riviera Theatre, you can balance tranquility and urban exploration. Parking available.

Welcoming Evanston Home

We have a newly renovated suite awaiting your stay, perfect for one guest. This dedicated entry, private room + bathroom, and tree-lined street are in our quiet neighborhood in beautiful Evanston, just north of Chicago. As international travelers ourselves, we love hosting others from near or far! Enjoy a short walk to cafes, stores, mall shopping, parks, and restaurants. Easy free parking, convenient Uber / Lift rides, and public transportation are also here to make your stay enjoyable.

Great Location / Private Room in Lakeview

Enjoy easy access to everything from this perfectly located home base. Walking distance to Wrigley Field, The Vic, The Briar Street Theater (Blue Man Group), some of the cities best restaurants, bars and coffee shops, Advocate Illinois Masonic Medical Center, The CTA’s Red Line which takes you right downtown to the Loop, Depaul, Chinatown and a host full of other Chicago destinations. There’s really no need for a taxi or Uber with so much that is walkable or accessible from the red line.

UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)

Beautiful private house for share on quiet street in the heart of Uptown. Moments from Aragon, Green Mill, etc. Amazing neighborhood that's close to all! Quick to CTA (Red Line) & buses! Ample space here including private en suite bathroom. Other amenities include: WiFi, private TV in rooms, private fridge/microwave in rooms, washer/dryer access, back deck with grill, and gated parking if needed —ask please. External security cameras in both front /back yard areas for added guest safety.

The Uptown Studio Retreat

Stay in the heart of Uptown Chicago in this bright, modern studio just steps from Lake Michigan, public transit, and endless dining options. Located above a lively late-night bar, you’ll be close to the action with the convenience of everything right outside your door. Inside, enjoy a comfortable queen bed, a fully equipped kitchen, and stylish brick accents that give the space its warm character. Perfect for guests looking to experience Chicago’s vibrant neighborhood energy.

Updated full floor urban retreat private suite

Our newly remodeled private urban retreat with vaulted ceilings, features a private en suite bathroom that takes up the entire 3rd floor. Located in Andersonville (2nd coolest neighborhood in the world according to Time Out), we are steps from the train, beaches, great dining and shopping. Walking distance to the Aragon Ballroom and Riviera Theater. Close to Wrigley Field/Cubs. It's a quick train ride downtown or Evanston. Lots of free street parking!

Full Luxury Home in Wrigleyville

Enjoy your stay in Chicago like a TRUE "Chicagoan" would. Enjoy the charm of exposed brick in a historic Chicago brick walk-up building steps away from the Left Field wall of Wrigley Field. Home features a king bed, pull-out couch, Amazon Fire TV, and exposed brick. This quiet tree-lined street is walking distance to the lake, Red Line, Clark Street bars / restaurants and Wrigley Field.

Private studio near Wrigley

Getting to all major destinations is key while also coming back to a quiet neighborhood. Only a few steps from public transportation. The unit is attached to a single family home with your own private entrance and access to the backyard that has a gas grill and fire pit. We are a 1 mile walk to Wrigley Field. Also had a pull out couch if need additional sleeping space.

Uptown Studio Gem

Enjoy the best of Chicago’s North Side from this bright and comfortable studio apartment located on W Montrose Ave. Nestled between the lively Uptown and Lakeview neighborhoods, this spot is perfect for solo travelers, couples, or remote workers looking for a peaceful, well-connected place to stay.