Holiday rentals in 31st Street Harbor

4.91 out of 5 average rating, 123 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Superhost

Home in Chicago

4.89 out of 5 average rating, 28 reviews

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home nestled in the historic Bronzeville neighborhood. This beautiful residence boasts enchanting décor and well-appointed living spaces that promise a memorable stay. Its minimalist charm and comfortable setup reflect a contemporary/modern aesthetic, making it an irresistible choice for guest. Just 6 mints from the downtown, 20 mints from Midway Airport, and 4 mints from McCormick Place & UOC, it's perfect for any length of stay.

Top guest favourite

5 out of 5 average rating, 11 reviews

Designer Garden Unit in Bridgeport

Welcome to Bridgeport! You're a short walk from the best coffee shops, vintage stores, cocktail bars, art galleries, parks, restaurants, and Rate Field, the home of the White Sox! The neighborhood has so much to offer! Just minutes from Chinatown, McCormick Place, and 10 minutes to downtown Chicago! Be sure to check out my guidebook for recs! I look forward to hosting you! -Free street parking -easy Uber/Lyft 24/7 -easy access to public transit -15-25 mins from Midway -30-45 mins from O'Hare

4.92 out of 5 average rating, 71 reviews

Guest house in Chicago

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept multipurpose space, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transportation - 5 minute walk Lakefront - 10 minute walk University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles Mccormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, great access to expressways to get anywhere in the city.

4.88 out of 5 average rating, 250 reviews

Historic Coach House Cottage

Historic Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Ideal for relaxation, peace & quiet. Cozy and quaint with flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants in Hyde Park. Seconds from park, walking track and playground. 15 Minutes from downtown and Magnificent Mile. Local transportation and bike rental within blocks.

4.75 out of 5 average rating, 327 reviews

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.

Superhost

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

4.99 out of 5 average rating, 109 reviews

Loft in Chicago

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Superhost

4.94 out of 5 average rating, 17 reviews

Stay & Play: Sox, Bears & Lake!

This spacious 1 bed 1 bath Garden unit is perfect for exploring Chicago! Located in a family-friendly historic Chicago neighborhood next to White Sox Stadium, Soldier Field, and a 15-minute walk to Lake Michigan. It's also just a 10-minute drive to the Magnificent Mile for Chicago's best shopping and dining. The unit features a 75-inch TV, darts, mini fridge, microwave, and complimentary snacks and coffee. A cozy spot for sports fans and city explorers, alike!

Top guest favourite

Home in Chicago

4.97 out of 5 average rating, 75 reviews

NEW! Lake & Skyline Views Kenwood CuldeSac+Parking

Modern luxury awaits you in this Urban Oasis. New construction with all new finishes and stylish decor. Great natural light, free parking, views of Lake Michigan and the Chicago Skyline, nestled on a culdesac. Take advantage of countless attractions that the Windy City has to offer. A few minutes from Navy Pier, Downtown, White Sox Stadium, Museum Campus, University of Chicago, 31st Street and Oakwood Beach Perfect for photos and filming!

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!

4.88 out of 5 average rating, 50 reviews

Guest suite in Chicago

Comfy suite w/ steam shower near McCormick Place

Welcome to the landmark! Our well appointed studio space is situated in the historic Calumet-Giles-Prairie District; minutes from McCormick Place, Sox Park, Wintrust Arena, IIT, and downtown. Walk to 31st St Beach, bike to Museum Campus. Perfect for business or leisure; enjoy steam shower, Wi-Fi, smart TV, and full kitchen. Easy access to major highways and public transit.

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Other great holiday rentals in 31st Street Harbor

5 out of 5 average rating, 3 reviews

Room w/ Private Bath | Chicago

MarkRating, 5 stars2 weeks ago

Daniel was a fantastic host! He made me so comfortable in his home and yet, I had all the privacy I could want. He described the area in great detail and offered lots of good suggestions on where to go for different meals. His place was exactly as described in his listing and the photos were an exact match. Daniel was a really friendly, helpful guy and I would stay at his place again any time! Thanks, Daniel!

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.

5 out of 5 average rating, 17 reviews

Private bath Hyde Park UChicago x2

MichaelaRating, 5 stars4 days ago

The room was clean, instructions to get in the apartment are very easy to follow. Great communication with the owner. The apartment is located very close to the public transportation.

4.85 out of 5 average rating, 119 reviews

Hyde Park/UC Newly Renovated Private Room #1

MarcianoRating, 5 stars2 weeks ago

Great stay at Andy's place. Listing is accurate to the description. Place is clean, private room and shared bathroom has all the essentials. Roommates were very private so I felt like I was free to stay in the common areas without much disturbances. Andy himself was very professional and responsive to my messages. Check in was very easy. I would recommend Andy's place and would definitely stay here if I am in town again for a conference. Thank you for a very peaceful and pleasant stay, Andy!

Shared hotel room in Chicago

4.71 out of 5 average rating, 28 reviews

Convenient Stay In The Heart of River North

RyanRating, 5 stars2 weeks ago

Loved staying here! It’s in such a great, walkable area and the design of the hotel is very impressive. Felt right at home!

4.87 out of 5 average rating, 47 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.

Hotel room in Chicago

4.63 out of 5 average rating, 38 reviews

modern design with VU Skyward rooftop bar

TaviasRating, 5 stars2 weeks 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.