Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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Superhost

Flat in Lake View

4.82 out of 5 average rating, 314 reviews

Sophisticated, Historic & Comfy Flat near Wrigley!

Down comforters, nice towels and linens + stylish design and comfort You will have access to the entire space - 4 bedrooms, 2 bathrooms, living room, dining room, kitchen, back deck, and back yard. Send me a text or call. This home is in the heart of it all, just a 10-minute drive to the lake, beach, and Wrigley Field. A strip mall is close by with different food outlets. Uptown's Green Mill Jazz club, Riviera Theatre, and Aragon Ballroom are a short bus ride away. The Montrose Brown Line stop is a 7 minute walk directly west. The #22 bus is a 2 minute walk away and takes you to Wrigleyville (south 10 mins) and Andersonville (North 10 mins) The #78 bus stops right outside and can take you Montrose Beach (east 10 mins) or to the Blue Line airport transfer (west about 25 minutes) Free Street parking on Montrose or Ashland is usually available. Deluxe California King Blowup Mattress available for living room. Very comfortable.

Guest favourite

Flat in Lincoln Park

5 out of 5 average rating, 239 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Guest favourite

Guest suite in West Town

4.96 out of 5 average rating, 331 reviews

Secret Garden | Noble Square | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Guest favourite

Flat in Edgewater

4.89 out of 5 average rating, 92 reviews

Adorable Private Edgewater Suite

Cozy exposed brick, garden unit on a quiet street, perfect for relaxing after a night out in the city! Comfy, queen-sized bed, full kitchenette and gated private side entrance so its the perfect spot for your trip to Chicago! We are right by the exciting nightlife of Andersonville and a 10 minute walk to the beach/start of the Lakefront trail. Public Transit is close and easily accessible, the redline "L" can get you downtown in a half-hour train ride. Close to Loyola University, Go Ramblers!

Guest favourite

Flat in West Lake View

4.93 out of 5 average rating, 147 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Guest favourite

Flat in East Rogers Park

4.88 out of 5 average rating, 114 reviews

Rock Star Beach Pad on Lake Michigan with parking

Live like a Rock Star! Stay in a celebrity 2br 2bath apartment with its own beach on Lake Michigan. The apartment is on the 2nd floor in a walk-up building consisting of 5 short-term rental apartments. 2 apartments on each floor. The apartment has direct water views with a shared porch with a -Free Onsite Parking with EV Charging Station -Steps away from parks and minutes to restaurants universities and shopping -Less than 20 min drive to Wrigley Field, Downtown Chicago, and museums.

Guest favourite

Home in Lake View

4.88 out of 5 average rating, 165 reviews

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

Guest favourite

Home in Wrigleyville

4.91 out of 5 average rating, 172 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Superhost

Flat in Lake View

4.85 out of 5 average rating, 104 reviews

Chic Penthouse In Perfect Wrigleyville Location

Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, Lake Michigan, Lincoln Park, top notch neighborhood restaurants, pubs, and entertainment, and many more! With so much to do in the area and easy access to public transit you're sure to have jam-packed days of exploring and enjoying the city. After a long day, come back to this peaceful apartment to relax, recharge, and prepare to do it all again tomorrow. Book today!

Superhost

Flat in Logan Square

4.91 out of 5 average rating, 11 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: -Uber-fast Wifi streaming, -Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches for living - Designed for an aristocratic feel - The touristy 606 Trail access 100ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Superhost

Home in Homewood

4.91 out of 5 average rating, 118 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Superhost

Apartment in Lincoln Park

4.81 out of 5 average rating, 150 reviews

Massive Old Town Home Steps to Wells St & Beach

Massive Old Town home steps to Wells St & Beach - Sleeps 20 Guests Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking an extra day. Guests between the ages of 18-24 are permitted to book on an exception basis only. In your inquiry please provide your age, reason for booking and who will be staying with you. Local guests are permitted to book on an exception basis only.