Vacation rentals in Near North Side

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Deluxe King Room · Juliette Balcony · Sono B&B

You’ll be charmed by this private guest room inside The Sono Chicago Bed and Breakfast, a newly built boutique B&B in the heart of Chicago’s historic Old Town. This listing is for one private king room with a Juliette balcony within a shared bed and breakfast. Guests enjoy their own bedroom and ensuite space. Complimentary breakfast is included each morning. We’re located on a quiet, tree-lined street and offer cozy accommodations, warm hospitality, and a welcoming sense of community.

Zen in La Grange Park

Relax. Recharge. Explore. Welcome to Zen, your peaceful retreat in beautiful La Grange Park. This charming 2-bedroom ranch offers the perfect blend of comfort and convenience with spacious living areas, a fully fenced backyard, and an attached 2-car garage — ideal for families, friends, or extended stays. Nestled in a quiet neighborhood, you’ll enjoy a relaxing atmosphere while being just minutes from nearby trains and bus stations that provide easy access to Downtown Chicago.

Private Room in Theatre District

Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations. Make the most of your stay with our top-notch services and on-site restaurant that offers classic American cuisine. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

Large private room w/ shared bathroom in Boystown!

Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Arlo Chicago

Step into the city king room where inspiring views of downtown and a spacious cozy king bed invite you to relax in style. Enjoy smart amenities like a Nespresso coffee machine, a 55 inch flat screen TV, a smart fridge and a work desk. Contemporary luxury design and thoughtful details like a hand held steamer hair dryer and laptop sized safe make this a perfect home base whether you are exploring the city or enjoying a quiet night in.

Riu Plaza Chicago

The deluxe family king room is a perfect choice for families visiting Chicago, offering plenty of space and comfort for your city getaway. Enjoy amenities like central heating, air conditioning, and an in-room safe to ensure a relaxing stay. A small fridge, coffee maker, and sofa bed add extra convenience for your family. Practical touches such as a shower, hairdryer, and iron are also included for your comfort.

Close to Navy Pier + Restaurant. Bar. Gym.

Tucked just off the Magnificent Mile, Hotel Saint Clair gives you front-row access to Chicago’s must-sees—think Navy Pier, Millennium Park, and late-night eats around the corner. Sip your morning coffee, grab your camera, and hit the lakefront in minutes. The rooms are pet-friendly, WiFi’s on the house, and everything you want to see is walkable. It’s your laid-back launchpad for big city adventures.

Millennium Knickerbocker Hotel Chicago, Standard...

Standard room offers a tastefully decorated space with a plush king bed designed for your comfort and relaxation. Enjoy modern amenities like WiFi, smart TV and an in room safe along with coffee and tea making facilities. Thoughtful touches create a welcoming atmosphere for both work and leisure making it an ideal choice for any traveller. Unwind and recharge in style during your stay.

The Emily Hotel

Deluxe king features a classic king size bed, a flat screen television, a fully stocked minibar, a custom bluetooth radio, and complimentary wifi for a comfortable stay. Enjoy bathrobe, Malin & Goetz bathroom amenities, and free toll free calls for added convenience. Clean lines and thoughtful touches create a stylish and relaxing retreat.

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.

Adorable studio style unit - Self check in ⚡️

Cozy studio style unit close to downtown Chicago, ORD airport, Wrigley Field, Old Orchard Mall, Northwestern University and much more! The unit has its own kitchen, full bath, Kurig coffee maker available and bottled water in the fridge for your use - all jam packed in this cozy secure space!