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Apartment holiday rentals in Old Town, Chicago

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Old Town, Chicago

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Flat in Park Ridge

4.79 out of 5 average rating, 425 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

Flat in Chicago

4.98 out of 5 average rating, 199 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

Flat in Wicker Park

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.

Flat in Lake View

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.

Flat in Avondale

4.86 out of 5 average rating, 527 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

Flat in Lincoln Park

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

Flat in Lake View

4.83 out of 5 average rating, 108 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

Flat in Lake View

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

Flat in Summit

4.89 out of 5 average rating, 102 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

Flat 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.

Flat 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!

Guest favourite

Flat in Wrigleyville

4.93 out of 5 average rating, 346 reviews

Seminary Flat 1 minute walk to Wrigley Field

Beautifully remodeled apartment steps from Wrigley Field and bars. Half block from the field and One block away from the Wrigleyville night life. The apartment is right next to all the action but just far enough for a quiet night sleep. You will be pleasantly surprised how quiet my block is one hour after the game ends. Walking distance to the beach and a block from the red line.

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Popular amenities for Old Town, Chicago apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Flat in Skokie

4.9 out of 5 average rating, 59 reviews

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

Guest favourite

Flat in West Lake View

4.95 out of 5 average rating, 105 reviews

Chic retreat near the best of Lakeview & Wrigley

Guest favourite

Flat in Wicker Park

4.94 out of 5 average rating, 102 reviews

Bright two bedroom garden apartment

Guest favourite

Flat in Lincoln Square

4.91 out of 5 average rating, 186 reviews

Comfortable Vintage North Side Retreat for 8

Guest favourite

Flat in Lincoln Park

4.95 out of 5 average rating, 111 reviews

Elegant Depaul Apt on Jonquil Park

Guest favourite

Flat in West Town

4.92 out of 5 average rating, 349 reviews

Spacious & private! Free parking! Great location!

Guest favourite

Flat in Irving Park

4.94 out of 5 average rating, 231 reviews

Cool and Modern Chicago Apartment near Transit

Flat in West Town

4.85 out of 5 average rating, 161 reviews

*Comfortable & Spacious Home Close to Downtown*

Private apartment rentals

Guest favourite

Flat in Oak Park

4.87 out of 5 average rating, 276 reviews

Cosmopolitan Nest in Oak Park North Side

Guest favourite

Flat in Near North Side

4.9 out of 5 average rating, 126 reviews

Modern 3BR with Private Rooftop & Free Parking

Guest favourite

Flat in Lincoln Square

4.79 out of 5 average rating, 289 reviews

Cozy Garden-Subterranean Apartment

Guest favourite

Flat in East Rogers Park

4.9 out of 5 average rating, 142 reviews

Private Garden Apartment GATED FREE Parking

Guest favourite

Flat in Avondale

4.98 out of 5 average rating, 103 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

Flat in Logan Square

4.8 out of 5 average rating, 138 reviews

Welcome Chez Moi

Guest favourite

Flat in Avondale

4.91 out of 5 average rating, 268 reviews

Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby

Flat in Roscoe Village

4.75 out of 5 average rating, 254 reviews

North Side Pied-à-terre

Apartment rentals with a hot tub

Flat in West Loop

4.82 out of 5 average rating, 74 reviews

Quiet but in the Heart of City walk Everywhere

Flat in The Loop

4.89 out of 5 average rating, 37 reviews

The Areal Oasis

Guest favourite

Flat in West Rogers Park

4.85 out of 5 average rating, 60 reviews

Spacious Beautiful Condo

Flat in Lake View

New place to stay

Lakeview Apt Sleeps 6 - Games - Minutes to Wrigley

Guest favourite

Flat in West Loop

4.96 out of 5 average rating, 23 reviews

Skyline Oasis: City & Lake Views

Guest favourite

Flat in Belmont Cragin

4.99 out of 5 average rating, 87 reviews

Belmont Pleasures - hot tub / arcade gaming room

Guest favourite

Flat in Irving Park

4.9 out of 5 average rating, 21 reviews

Cozy 2Bed 2Bath with Parking, Balcony &Jacuzzi

Quick stats about flat rentals in Old Town, Chicago

Total rentals
30 properties
Nightly prices starting at
$95 SGD before taxes and fees
Total number of reviews
3.6K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore