Holiday rentals in Chicago

5 out of 5 average rating, 25 reviews

Flat in Chicago

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

4.96 out of 5 average rating, 172 reviews

Home in North Park

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

4.98 out of 5 average rating, 156 reviews

Flat in Magnificent Mile

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

4.86 out of 5 average rating, 650 reviews

Flat in Oak Park

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

4.99 out of 5 average rating, 137 reviews

Flat in Humboldt Park

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

4.95 out of 5 average rating, 44 reviews

Flat in River North

River North | Private Balcony With In&Out Parking

Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, one-bathroom unit is perfect for corporate travelers and/or families looking for a stylish escape in downtown Chicago 🌆. 🌇 Rooftop Patio W/ BBQ 🍖 🚗 Free In/Out Parking - 5 Mins Walk To Garage 🌅 Private Balcony W/ Breathtaking Views 🛏️ 2 Bedroom | 1 Bathroom 👑 2 Queen Beds 🛏️ 1 Inflatable Airbed 👶 Portable Crib 📺 Netflix, Hulu, Disney Plus, and Prime subscription Included

5 out of 5 average rating, 11 reviews

Flat in Little Village

2B Midcentury Artist Loft w King Bed

Welcome to Casa D'Mi Amá, this vibrant mid-century loft style apartment is centrally located in Little Village, one of the most vibrant Mexican-American communities and thriving shopping district in Chicago. Our community is known for its colorful murals and hundreds of Latinx-owned businesses and restaurants. We are just 4 mile away from downtown & Midway airport, three miles away from Pilsen & UIC, with public transportation right outside your door making it easy to plan your visit.

4.82 out of 5 average rating, 756 reviews

Flat in Near North Side

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

4.78 out of 5 average rating, 142 reviews

Flat in South Loop

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

4.86 out of 5 average rating, 361 reviews

Flat in Lincoln Square

Renovated Designer Flat in Heart of Lincoln Square

Kick back with a fresh coffee and enjoy the designer touches of this renovated apartment, including marble worktops, wood floors and 1920s exposed brickwork. There are great courtyard views, while the memory foam mattress and super-sized sofa add real comfort. Lincoln Square is a quaint, family-friendly neighborhood. There's abundant German influence here, and great shops, restaurants, and bars line Lincoln Avenue. Downtown is 20 mins by train. Wrigley Field is close too.

Guest house in Wicker Park

4.98 out of 5 average rating, 40 reviews

Solar Victorian MCM Coach House

Immerse in solar-powered serenity amidst the bustling restaurant, shopping and nightlife scene of the Wicker Park neighborhood of Chicago. Large, loft-like and super sunny one bedroom includes full kitchen with new appliances, landscaped garden patio, and EV charging in an enclosed and attached garage space. All powered by a full array of high-efficiency rooftop solar panels. Five minute walk to the Damen Blue Line and the 606 Elevated Trail for cyclists and runners.

4.99 out of 5 average rating, 228 reviews

Flat in Chicago

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

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Popular amenities for Chicago holiday rentals

Kitchen

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Pool

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Stay near Chicago's top sights

O'Hare International Airport13 locals recommend

Wrigley Field155 locals recommend

United Center50 locals recommend

Millennium Park213 locals recommend

Navy Pier271 locals recommend

University of Chicago14 locals recommend

Other great holiday rentals in Chicago

Private room in South Side

5 out of 5 average rating, 15 reviews

Private bath Hyde Park UChicago x2

ParvaneRating, 5 stars1 week ago

I had a great stay at Sydney's place in Chicago. The room and the house were very good, clean, bright, and clearly recently refurbished with attention to detail. It felt comfortable and welcoming. Access to transportation was excellent, with easy connections to the subway, buses, and other transit options. That made getting around the city very convenient. Personally, I didn’t love the neighborhood, but that’s just a matter of preference, others may feel differently. Also, the check-in process was a little confusing on the first day as I got a bit lost coming from the subway, but everything went smoothly afterward.

5 out of 5 average rating, 132 reviews

Private room in Uptown

Easily accessible Uptown room

MarinaRating, 5 stars1 week ago

We absolutely loved starting at Cameron’s place! It was so clean, beautiful and in the perfect location for us. Cameron was so kind and helpful and really set the bar for what an Airbnb host should be. We would definitely book to stay there again!

Private room in Lake View

4.94 out of 5 average rating, 98 reviews

Fantastic Location / Private Room

AlexanderRating, 5 stars1 week ago

I had an incredibly good time with Tim. His apartment is extremely well connected and allows you to explore Chicago quickly. However, people who are light sleepers should be aware that the apartment is right next to a train line. Even though Tim provided earplugs, it can be noisy. Overall, however, I was very happy with the apartment.

4.81 out of 5 average rating, 54 reviews

Private room in Chicago

Cottage Crafts Room - Free Parking, 1 block to CTA

IvonneRating, 5 stars1 month ago

We loved Ryan's place, we were very comfortable, we really didn't feel right at home. The area is very quiet and easy to transfer. We look forward to returning soon.

Private room in Logan Square

4.98 out of 5 average rating, 60 reviews

Private bdr | Free garage parking | No fees

JessicaRating, 5 stars1 week ago

Brett is a lovely host, super on top of communication and really helpful! I enjoyed chatting with him about the various Chicago neighborhoods. Everything was clean and comfortable.

Private room in Norwood Park

4.95 out of 5 average rating, 63 reviews

+Safe Area-Laundry-42" TV-Mini Fridge + More!

VincentRating, 5 stars1 week ago

Joey’s place was exceptional. It was perfect for what I was looking for and needs. Hosts were very kind, understanding, and available upon any requests. Great recommendations and very helpful. Joey went out of his way to help me and made me feel very comfortable and I am grateful for his excellent hospitality. It was a very comfortable stay. I would highly recommend if searching for a reasonable price, close to many places in Chicago, and overall quality stay. Thank you Joey for all your help!

Private room in North Park

4.97 out of 5 average rating, 35 reviews

Lovely master bedroom with private bath

NicoRating, 5 stars1 week ago

Hi , It all worked out wonderfully. The apartment and the location was exactly as stated in the listing. It's very clean. The cat Loki is very sweet and always greets you very nicely. Samuel is very friendly and always has a few tips in store, e.g. where to eat. All in all a wonderful stay and a very nice AirBnb which we will definitely visit again.