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Apartment holiday rentals in Downtown Chicago

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Top-rated apartment rentals in Downtown Chicago

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Apartment in Park Ridge

4.79 out of 5 average rating, 419 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

Guest favourite

Apartment in Chicago

4.99 out of 5 average rating, 197 reviews

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

Enjoy Chicago in style! This newly renovated apartment on Chicago’s west side offers high end finishes and all of your basic needs. This unit features 2 spacious bedrooms and one bath with a jetted soaking tub so that you can unwind after a long day of exploring our beautiful city. Commuting around the city from this location is super easy! You’re only one block away from the CTA blue line train, CTA #7 Harrison Bus and I-290! The train and interstate can get you downtown in just 15 minutes!

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 135 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Apartment in Chicago

4.82 out of 5 average rating, 125 reviews

Wrigleyville 4-Bed with Tons of Sunlight

The is a very comfortable spacious apartment with high ceilings, abundant sunlight. The kitchen and bath were recently remodeled. The location is the best of both worlds as it's nestled on a quiet side street surrounded by historic mansions yet is a quick walk to Wrigley Field, public transit, and the lake. Just a few short blocks to all the nightlife, shopping, arts/entertainment, and restaurants Wrigleyville has to offer. 20 minutes via EL train to Downtown, Mag Mile, Grant Park, etc.

Apartment in Chicago

4.86 out of 5 average rating, 523 reviews

Logan Square Lookout

Great 1st floor apartment along a tree lined street with free street parking. Has 2 cozy bedrooms with a spacious living room and kitchen. On site laundry. Great back yard with garden area. In the super nice Logan Square neighborhood with cool bars and award winning restaurants. Friendly safe neighborhood with lots to do. Quick walk to the Blue Line gets you Downtown or out to O'Hare. I own the building which consists of 3 apartments. So always nearby. permit parking is provided

Guest favourite

Apartment in Chicago

4.89 out of 5 average rating, 131 reviews

Sounds Of The City

Fun and lively location! Cozy one-bedroom "stumbling distance" from McGee's Tavern and Grille, as in right upstairs. It’s pretty peaceful during the day except some train noise but the popular bar below ranges from a little noisy to pretty loud at night. Lincoln Park is an upscale, safe & convenient area. Walking distance to cafes, dining, pubs, parks, transportation, Lyft bikes, yoga, fitness, Amazon, etc. Weekends draw the biggest crowds and noise. Free street parking.Easy Uber/Lyft

Apartment in Chicago

4.84 out of 5 average rating, 106 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!

Guest favourite

Apartment in Chicago

4.93 out of 5 average rating, 505 reviews

Victorian Home meets Mid-Century Modern Decor

This private studio-apartment (also known as an in-law suite) is the first floor of my restored Victorian home. The apartment has its own private ground floor entrance located in a beautiful neighborhood within the designated historic district called Old Town. It's a block from local train transportation, a bus stop is located across the street, and is a 5 minute walk to the lake. Great restaurants abound in the neighborhood. Maximum occupancy of 2 is the legal limit.

Guest favourite

Apartment in Chicago

4.93 out of 5 average rating, 193 reviews

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Guest favourite

Apartment in Summit

4.9 out of 5 average rating, 100 reviews

2BR Apartment Near Chicago

New Beautifuly Renovated Modern 2BR Apartment sitting right aside Hanover Park with Playground, Large Field, Swings, & Basketball Court. In a Peaceful neighborhood near the downtown Chicago area. 10 minute drive from Midway Airport and a 20 minute drive to lakeshore drive, Millenium Park, beaches, restaurants, museums, and more. You'll be pleased and delighted to stay here among its Cozy living room, Beautiful Kitchen and Serene Rooms!

Guest favourite

Apartment in Evanston

4.97 out of 5 average rating, 106 reviews

Charming one bedroom apartment

Downtown Evanston. Cozy quiet area. Lovely studio 1-bedroom apartment. Ideal for a couple or business travelers. One queen size bed. TV & WiFi, microwave, AC & dishwasher. Free off-street parking. Close walk to Northwestern U, Lake Michigan, several supermarkets & many restaurants. Minutes to Metra, Davis & Dempster CTA stations. About 40 minutes to downtown Chicago on CTA Purple Express & less time on Metra. Non-smoking.

Apartment in Evanston

4.82 out of 5 average rating, 169 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!

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Weekly apartment rentals

Apartment in Skokie

4.9 out of 5 average rating, 59 reviews

Charming 2 bed/1 bath apt- walk 2 train/store/rest

Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 104 reviews

Chic retreat near the best of Lakeview & Wrigley

Guest favourite

Apartment in Chicago

4.94 out of 5 average rating, 102 reviews

Bright two bedroom garden apartment

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Apartment in Chicago

4.91 out of 5 average rating, 186 reviews

Comfortable Vintage North Side Retreat for 8

Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 111 reviews

Elegant Depaul Apt on Jonquil Park

Apartment in Chicago

4.85 out of 5 average rating, 161 reviews

*Comfortable & Spacious Home Close to Downtown*

Guest favourite

Apartment in Chicago

4.82 out of 5 average rating, 253 reviews

BERNARD CHATEAU - LOGAN SQUARE

Guest favourite

Apartment in Chicago

4.89 out of 5 average rating, 171 reviews

Private 2 Bedroom Retreat

Private apartment rentals

Guest favourite

Apartment in Chicago

4.91 out of 5 average rating, 123 reviews

Modern 3BR with Private Rooftop & Free Parking

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Apartment in Chicago

4.9 out of 5 average rating, 142 reviews

Private Garden Apartment GATED FREE Parking

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Apartment in Chicago

4.98 out of 5 average rating, 103 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

Guest favourite

Apartment in Chicago

4.91 out of 5 average rating, 268 reviews

Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby

Apartment in Chicago

4.75 out of 5 average rating, 253 reviews

North Side Pied-à-terre

Apartment in Chicago

4.77 out of 5 average rating, 267 reviews

Classic 2 Bedroom Roscoe Village Apartment

Guest favourite

Apartment in Evanston

4.84 out of 5 average rating, 244 reviews

Adorable 1BR apartment near Northwestern

Apartment in Chicago

4.88 out of 5 average rating, 275 reviews

Chic, Modern Lincoln Square Condo with Open Layout

Apartment rentals with a hot tub

Apartment in Chicago

4.82 out of 5 average rating, 72 reviews

Quiet but in the Heart of City walk Everywhere

Apartment in Chicago

4.6 out of 5 average rating, 5 reviews

City Life, Neighborhood Comfort - Studio

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 23 reviews

Skyline Oasis: City & Lake Views

Apartment in Chicago

4.67 out of 5 average rating, 3 reviews

Central 1BR Retreat – Cozy & Inviting Near Loyola

Guest favourite

Apartment in Chicago

4.99 out of 5 average rating, 85 reviews

Belmont Pleasures - hot tub / arcade gaming room

Guest favourite

Apartment in Chicago

4.91 out of 5 average rating, 22 reviews

Lake, City, & River View Condo

Guest favourite

Apartment in Chicago

4.89 out of 5 average rating, 19 reviews

Cozy 2Bed 2Bath with Parking, Balcony &Jacuzzi

Guest favourite

Apartment in Chicago

4.87 out of 5 average rating, 440 reviews

Checkerboard Studio with Private Outdoor Hot Tub and Yard

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