Hotel holiday rentals in North Side

4.89 out of 5 average rating, 9 reviews

Art-inspired design and Malin+Goetz bath products

Welcome to The Emily Hotel - a boutique hotel experience in the heart of Chicago’s Futon Market inspired by the belief that art changes the way we look at the world. With comfortable, modernist rooms and design forward spaces featuring a curated collection of art from near and far. We’re home to 8,000 sq ft of unique event space and a collection of culinary and experiential destinations including Fora. A blend of functionality and style. Just 2.5 miles from Grant Park/Lollapalooza 2025!

4.8 out of 5 average rating, 162 reviews

All-glass gem by Chicago architect Harry Weese

Designed by renowned Chicago architect Harry Weese, Swissotel Chicago is an award-winning luxury hotel overlooking the Chicago River and Lake Michigan, and just steps from the Magnificent Mile. The distinctive 4-diamond, all-glass hotel offers spectacular wrap-around views from Navy Pier to Millennium Park, 662 guest rooms and suites, five premier ballrooms, state-of-the-art penthouse fitness center, and spotless European-style service. Pet Friendly, $50USD/night, $250 refundable deposit.

4.79 out of 5 average rating, 236 reviews

Hotel Quality Meets Local Living Deluxe Studio 3B

Quaint, cozy and 100% private, our overnight Guest Rooms offer honest to goodness pillow top mattresses with 500 thread count linens. Comfortable, simple and clean, additional features include: Private glass and marble showers, comfy chair, desk, custom woodworking and molding abound. Carpeted floors, oriental rug, natural light, modern and vintage décor/furnishings, high speed internet access, soft comforters and thirsty towels. Note there are no TV's in rooms and no elevator.

4.8 out of 5 average rating, 194 reviews

Spacious Hotel Room in The Loop

Just steps away from the famed shopping on State Street, this boutique hotel is located inside the Nederlander Theater building in the Chicago Loop Theater District. The hotel features on-site dining, state-of-the-art business services and modern guest rooms with free WiFi. Every room at Cambria Hotel Chicago Loop/Theater District provides a 49-inch flat-screen HDTV and a large work space with a desk and ergonomic chair. Select rooms also offer plush lounge seating.

4.71 out of 5 average rating, 75 reviews

Private room in Chicago

$N-PrivateRoom+Safe North Area+Free Street Parking

Relax by yourself or with a friend or partner by staying at this peaceful place. A modern and classic art decorated apartment. You can rent this one or even the whole apartment if available. There is an extra sofabed in the living room or extra twin bed available for you to use if your party is larger than 3 people and if you reserve both rooms. In this unit you share the living room, kitchen and bathroom when renting only one private bedroom.

5 out of 5 average rating, 6 reviews

Modern design and smart amenities

The city’s hottest new hotel, formerly Hotel Julian, puts you at the heart of downtown Chicago, steps from iconic Millennium Park. Our guest rooms feature modern design and smart amenities, with a new take on the old soul of the landmark 1916 Atlantic Bank building. Come and experience Chicago’s then and now and make us your home base for today’s urban adventures. Just one mile from Grant Park where Lollapalooza 2025 will be held!

4.94 out of 5 average rating, 78 reviews

Light-flooded rooms and city views

The Hoxton, Chicago feels like a home away from home, with its comfy hotel rooms, great food and a rooftop to soak up some rays in the heart of Fulton Market District, one of Chicago's most creative neighborhoods. All rooms come with mid-century furnishings, modern bathrooms, and warehouse-style floor-to-ceiling windows to show off Chicago in full. Just 2.2 miles from Grant Park where Lollapalooza 2025 will be held!

4.93 out of 5 average rating, 268 reviews

Hotel room in Rosemont

Relaxing Standard Room l Free Airport Shuttle

Explore the charming neighborhood of Rosemont just outside our doors. Attractions await you: ✔ Offers a 24-hour front desk, airport transfers, an ATM and free WiFi throughout the property. ✔ Enjoy indoor pool or use the business centre that offers printing, copying and fax services. ✔ Breakfast included. Monday to Friday from 6:30AM to 9:30AM, and on Saturday and Sunday from 7:30AM to 10:30AM.

4.91 out of 5 average rating, 75 reviews

King Room in Boutique Wicker Park B&B

Modern guest room located on the main floor just a block away from great dining, vintage and boutique shopping, art galleries, cool cafes and vibrant nightlife. The Ellen King guest room is one of 9 rooms within the Wicker Park Inn, a newly renovated, boutique Bed and Breakfast offering high quality yet affordable accommodations in a hip & trendy neighborhood.

4.82 out of 5 average rating, 89 reviews

Sweeping skyline views from the 40th floor

The moment you step into your spacious ‘home away from home’ on our 40th floor, you’re sure to envelope yourself in a view that takes your breath away. Our Deluxe King room offers lofty ceilings, an oversized marble tub, and wet bar- for your enjoyment. Just 5 blocks from Grant Park where Lollapalooza will be held!

Hotel room in Bloomingdale

4.8 out of 5 average rating, 83 reviews

Renovated Comfortable Room l NO Cleaning Fee

Welcome to Courtyard Bloomingdale Whether you're traveling for work or leisure, our newly renovated Marriott hotel in Bloomingdale, IL comes fully equipped to make your stay exceptional. Our convenient location makes it easy to spend time at Stratford Square Mall or go explore the sights of downtown Chicago.

Casa particular in Chicago

4.86 out of 5 average rating, 152 reviews

Studio apartment for 2 people maximum, comfortable and clean, very central with multiple access roads, urban transport and proximity to the train station, a variety of restaurants and shops.

Enjoy the simplicity of this accommodation located in a very central and quiet area, with easy access and very nice people. In addition to this, it has a variety of shops and restaurants nearby. We are very interested in cleanliness for the utmost convenience. Vehicles are parked on the street at no cost.

Holiday rentals for every style

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Popular amenities for hotel rentals in North Side

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Pool

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Family-friendly hotel rentals

4.91 out of 5 average rating, 35 reviews

Spacious 2BR near concert venues, Wrigley Field

tatiannaRating, 5 stars10 months ago

Rick’s place was great. Everything matched the photos. Location was great. Easy access to transportation if needed. Concierge was very helpful and friendly as well. Would stay here over and over again

4.85 out of 5 average rating, 20 reviews

Vibrant Andersonville 2BR w/ in-unit laundry

CourtneyRating, 5 stars83 months ago

This place was perfect for a week in Chicago with family! The space was as described, beautiful and sparkling clean, and communication with the host/staff was quick and easy. Having a 24-hour concierge and sundries for sale in the lobby was fantastic for any questions or snack/drink needs. And the Andersonville neighborhood is such a fun place to explore, with lots of great restaurants and shops!

4.98 out of 5 average rating, 44 reviews

Bright 1BR w/ shared Roof Deck, close to beach

TylerRating, 5 stars29 months ago

FANTASTIC Andersonville place to stay, walkable to all the best the neighborhood has to offer! Rick is super responsive, helpful, kind, and generous! Highly recommended, and hope to return soon :)

4.67 out of 5 average rating, 6 reviews

1BD/1BA steps away from local shops, entertainment

SusanRating, 5 stars34 months ago

A wonderful place, clean, well equipped, friendly, and located in a great neighborhood. We will return the next time we go to Chicago!

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Hotel rentals with a pool

Hotel room in Oakbrook Terrace

4.37 out of 5 average rating, 60 reviews

Your Oak Brook Escape| Free Parking & Pet-friendly

SunghwanRating, 5 stars2 weeks ago

It was a very convenient location for the airport with many restaurants and shopping centers around. The room was very clean and comfortable as well. Highly recommended.

Hotel room in Rosemont

4.53 out of 5 average rating, 34 reviews

Close To Chicago O'Hare Airport | Free Breakfast

EricRating, 5 stars2 weeks ago

everything was nice 😊

4.5 out of 5 average rating, 4 reviews

120-yr-old landmark with floor-to-ceiling views

AndreaRating, 5 stars9 months ago

The location is amazing! Extremely walkable to the lake & the river. So many places to eat & shop nearby. This room is a Superior king room, which isn’t noted in the listing, so look it up on their website; where you may even get a better rate and choose the type of room you’d prefer. It is quite small @337sq ft, even for just 2 people, but a nice room nonetheless. There is no dresser, just a closet with 2 smaller drawers, which worked ok for us. Full size lighted mirror, a shower & soaking tub (!!!) The pillows were all down feather or like.They did have water stations on 3 of the floors to fill your bottles, a great feature. The rooftop bar had delicious tapas and craft cocktails and a beautiful view of the city and lake. Paid $386 a night at the end of August & Labor Day wknd. The staff were extremely friendly. Overall, we enjoyed our stay very much! Would def stay again, but would book through Viceroy directly and get a lake view room that is larger.

4.88 out of 5 average rating, 8 reviews

Comfort and Relaxation! Parking, Near Navy Pier

DanyelleRating, 5 stars11 months ago

Clean hotel, beautiful room and area. Lots in walkable distance and friendly staff! Already at looking at coming back.

4.65 out of 5 average rating, 37 reviews

modern design with VU Skyward rooftop bar

TaviasRating, 5 stars1 week ago

I arrived earlier than my booking time and they were available to get me a room. It was right across the street from the event I was going to as well.

Hotel room in Westmont

4.44 out of 5 average rating, 36 reviews

King Bed with breakfast included

JasonRating, 5 stars2 days ago

perfect for a night’s stay. will definitely book again.

Hotel room in Schaumburg

4.29 out of 5 average rating, 14 reviews

Sparkling clean and quiet hotel!

DarleneRating, 5 stars1 month ago

This Air B&B is in the Radisson. it is an older hotel but very clean. There was a party going on in the lobby but we never heard a sound from our hotel room. The room was very clean. The bed was very comfortable. there was a fridge which was larger than what you usually see in hotel rooms. All in all, very nice and well worth the price.