Holiday houses in Grant Park, Chicago

Private room in East Pilsen

5 out of 5 average rating, 121 reviews

Urban Oasis Pilsen - guest room in townhouse

Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, TV den, and balcony.

4.75 out of 5 average rating, 327 reviews

Apartment in Bridgeport

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

Private room in River North

4.88 out of 5 average rating, 614 reviews

Chicago Speakeasy-Style Loft Space (Room 1A)

Welcome to our Chicago Speakeasy-style loft space. Built in the early 1900s, our two-floor loft provides a unique experience in the heart of River North. We have six individual private rooms and baths with a large common area, full kitchen and art gallery. Centrally located River North Chicago is a go-to district with a lively night scene, and a wide variety of restaurants, bars and clubs. ALREADY BOOKED? If this room is unavailable, check out my profile to see our other listings!

Loft in Pilsen Historic District

4.7 out of 5 average rating, 142 reviews

Studio with View of Skyline in Heart of Pilsen

Explore Pilsen and the beautiful City of Chicago in this unique Loft Style Studio apartment with a view of the Willis Tower and in the Heat of Pilsen. Apartment features a Roku TV with Wifi, private entrance, open layout, closet, bathtub with handheld shower head. 1 queen bed and a sofa bed couch, no kitchen but does have a fridge. No Private Parking, just street parking . Located near major transportation, Divvy Bike Station across the street, 10 minutes from Downtown Chicago.

Apartment in Near South Side

4.78 out of 5 average rating, 146 reviews

McCormick Place Studio/parking/sleeps up to 4

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Queen size air mattress 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

5 out of 5 average rating, 4 reviews

Apartment in Berwyn

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

Apartment in Pilsen Historic District

4.87 out of 5 average rating, 266 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

Private room in Streeterville

4.95 out of 5 average rating, 385 reviews

A+ location by Mag Mile, views, large sunny room

Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. Apartment is shared with single host (covid-vaccinated), happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/respectful host, Flexible luggage policy, fast wifi)

Guest suite in North Center

4.97 out of 5 average rating, 121 reviews

Modern Garden Apartment in Lincoln Square

Welcome to our stylish and updated one-bedroom apartment located in a classic brick building in Lincoln Square. Perfect for solo travelers or couples, the space features a comfortable queen bed and a bright, modern interior. Just a short walk to the Brown Line and steps from Lincoln Square’s cozy shops, top-rated restaurants, and vibrant local culture. Wrigley Field, downtown attractions, and Lske Michigan are easily accessible by bike or train.

Apartment in Chicago

5 out of 5 average rating, 3 reviews

Sunny Penthouse - Oakwood Beach

Gorgeous top floor 2 bedroom 2 bathroom condo in Bronzeville. It has high ceilings with lots of natural light. The kitchen is fully equipped with everything you need to cook a delicious meal. Plus, there are many food options nearby. Enjoy a 15 minute walk to the lake front and Oakwood beach. Centrally located near downtown, Solider Field, Rate Field, Field Museum, The Art Institute of Chicago, Chinatown, Hyde Park, and plenty more!

Apartment in Streeterville

4.7 out of 5 average rating, 280 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

4.97 out of 5 average rating, 74 reviews

Apartment in Albany Park

Bright Apartment

Relax in this sunny one-bedroom garden apartment in Albany Park (Not recommended for taller than 6'3"). Our apartment is perfectly located between downtown Chicago & O'Hare airport. You can go just about anywhere in the city in about 20-30 min as we are 5 minutes away from the Montrose blue line train stop, Kimball brown line train stop, and the I90/94 interstate. Please note, some areas have lower soffit ceilings.

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Popular amenities for Grant Park, Chicago holiday rentals

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Pool

Free parking on premises

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Stay near Grant Park, Chicago's top sights

Millennium Park213 locals recommend

Shedd Aquarium123 locals recommend

The Field Museum97 locals recommend

Adler Planetarium70 locals recommend

Willis Tower102 locals recommend

Chicago Riverwalk5 locals recommend

Other great holiday rentals in Grant Park, Chicago

Private room in Chicago

4.73 out of 5 average rating, 40 reviews

Bees Knees - Room 3

BernardoRating, 5 stars2 weeks ago

I really enjoyed my stay at this place and would definitely recommend it, especially for the value. It’s conveniently located near bus stops and small markets, which made getting around and grabbing essentials very easy. The host was always very responsive and helpful, which made the whole experience smoother. The apartment is well-equipped with many utensils—there were plates, glasses, a cooking area that worked well for meals, and even an iron and ironing board. It’s also relatively quiet, which was great for resting. There are a few minor details that could be improved, like a couple of broken light bulbs, some marks on the bathroom walls, and a creaky, uneven floor. I also missed having a few hooks in the bedroom. However, none of these were major issues or detracted from the overall quality of the stay. I would not recommend it for people with mobility issues due to the steep staircase, but all in all, a great place with excellent value and a very helpful host. Would stay again.

4.85 out of 5 average rating, 13 reviews

Private room in Uptown

Room in Vibrant Uptown Townhouse

ColleenRating, 5 stars2 weeks ago

I really enjoyed my stay. John was a great host and his place is beautiful and in a great location.

Private room in Chinatown

5 out of 5 average rating, 4 reviews

ChicagoChinatownCenterB

IsaacRating, 5 stars4 days ago

I cannot say enough good things about Zheng’s place. He is super attentive and always there to help. I will absolutely stay here again any time I visit the area. Highest quality for a very reasonable price.

Private room in South Shore

4.88 out of 5 average rating, 48 reviews

Yellow Room - South Shore Bungalow

GavinRating, 5 stars1 week ago

What a lovely place to stay. Lady Delia showed us her turtles and had a beautiful cat. She was very friendly and talkative. She drove us to get bus passes when we didn’t know where to get them. Jeffrey jump was a convenient bus to get from her place to the city very quickly. The bathroom had the window creaked open which made it smell like the coast in the mornings. The house is a historic bungalow which gave it a very different look and feel from what I’m used to. Spent some beautiful morning strolls along the neighborhood and got to see the beautiful architecture in the city; overall was worth what we paid.

4.78 out of 5 average rating, 188 reviews

Private room in Chicago

Cozy, Quiet, Private bathroom in private room

GabrielaRating, 5 stars2 months ago

Tanya was an incredible host! I had such a wonderful time at her place. She was very friendly and attentive and the place looked just as it was described. The place is 3min away from the bus and 5min away from the train station, so it’s very easy to get to the city.

Private room in Hyde Park

4.88 out of 5 average rating, 78 reviews

HydeParkC, UC, Chinatown, NavyPier, freeparking

SophiaRating, 5 stars3 weeks ago

My fiancé and I were in Chicago for the weekend for a short getaway. John’s place was perfect! It was quiet, extremely pristine, and offered free parking. The neighborhood was walkable and beautiful. The only thing I wish they offered was flexible check in. There was a time difference from Cincinnati to Chicago so we arrived earlier than expected. Overall, the stay is definitely worth the price!

Private room in North Park

4.97 out of 5 average rating, 38 reviews

Lovely master bedroom with private bath

LenaRating, 5 stars2 weeks ago

The apartment was beautiful and comfortable along with being in a nice spot just outside of downtown. Samuel was also very friendly and accommodating which is a definite plus! I would definitely stay with him again.