
Apartment holiday rentals in Near North Side
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Top-rated apartment rentals in Near North Side
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❤︎ 1,800ft² Parking ⎜ Workspace ⎜ W/D ⎜Full Kitch
• 1,800ft² | 167m² . My home is on the top floor of a four flat Itallian Brick Building . You have 3 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The fireplace is non working

Chic & Comfy • Close to Wrigley
Welcome to your comfy, cozy, cheerful hideaway in the beautiful Buena Park!☀️ Buena Park is a little-known gem. Our home is just blocks from the lakefront (4 blocks), Wrigley (6 blocks), and the major L-line in Chicago (1 block)...yet, you'd never know it given how peaceful and serene it is! We live here part-time, so rest assured you'll have everything you need for a comfortable and enjoyable stay. We ask you please respect our place, and that you enjoy the trinkets + personal items we have!

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)
Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

Christmas in the City- Holiday Duplex in Lakeview
Decorated thanksgiving-NYE. A front door walkup duplex condo in the heart of Lakeview neighborhood. A perfect cozy place for a holiday winter getaway. Surrounded by restaurants, bars and shops & just steps from the Wellington brown line train stop. Luxurious amenities such as designer toiletries, cooking oils/spices, cafe du monde coffee and various teas. Walk to nearby Wrigley, Lake, Lincoln Park Zoo or enjoy a cozy fire in private backyard adorned with planters full of wintery greenery.

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Lincoln Park Hideaway - 5 Min Walk to the Park!
800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Modern Izakaya Studio in Wicker Park
Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Great location. Free parking.
Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Old Town Modern | Elevator, Parking, Terrace
Welcome to Old Town Modern! Thoughtfully designed 2 bedroom/2 bath light filled condo with 13ft ceilings, private terrace and underground parking in a secure, elevator building. You'll be in the heart of the Old Town on Wells St with world-class dining right outside the door, short walk to Second City, Lincoln Park Zoo, and North Avenue Beach.

Beautifully Renovated 2BR in Historic Lincoln Park
In the heart of Lincoln Park's historic Arlington-Deming neighborhood and its tree-lined streets, this 3rd floor walkup is close to everything -- Lake Michigan, transportation, dining, nightlife, parks, and more! The recently renovated condo is perfect for families, with a large master suite and twin/full bunk in the second room.

River North Hideaway w/Amazing Views and Parking
In the heart of River North, this stylish retreat offers amazing city views, an ensuite bathroom for added comfort, and the convenience of an in-unit washer and dryer. Enjoy secure garage parking and a vibrant neighborhood full of top dining, nightlife, and shopping just steps away. Registration Number: R25000125394
Popular amenities for Near North Side apartment rentals
Weekly apartment rentals

Studio flat in the heart of Chicago's Gold Coast

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Lincoln Square Gem!

Newly updated 1BD/1B in Old Irving Chicago!

Susie's Space. 2BR easy parking & pet friendly

Luxurious River North 3BR/2BA- Free Onsite Parking

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Chic Home! Walk to Nightlife-Comedy-Restaurants!
Pet-friendly apartment rentals

Chic and Charming Vintage Condominium in Lincoln Park

Spacious 3BR • Great for Groups • Fast WiFi • Pets

Wrigley Residence in Iconic Wrigley Rooftop

Picture Perfect 3Bed Steps from Train and FLW

Luxuriously bright 3-bedroom condo: The Treehouse

Can't Beat This 2min Walk to Wrigley!

Large Remodeled Home in Lincoln Park, Sleeps 12!

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Apartment rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Just remodeled apartment close to airport and mall

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Best view and luxury style, Located in Downtown
When is the best time to visit Near North Side?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $170 SGD | $169 SGD | $180 SGD | $212 SGD | $221 SGD | $228 SGD | $228 SGD | $228 SGD | $187 SGD | $195 SGD | $181 SGD | $187 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about apartment rentals in Near North Side

Total holiday rentals
Explore 130 holiday rentals in Near North Side

Nightly prices starting at
Near North Side holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 5,260 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Near North Side holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Near North Side rentals

4.8 Average rating
Near North Side stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Near North Side’s top spots include 875 North Michigan Avenue, Chicago Riverwalk and Museum of Contemporary Art Chicago
Destinations to explore
- Rentals with a fireplace Near North Side
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- Flat rentals Near North Side
- Rentals with a patio Near North Side
- Rentals with lake access Near North Side
- Rentals with a sauna Near North Side
- Rentals with a firepit Near North Side
- Rentals with breakfast Near North Side
- Rentals with a cinema Near North Side
- Waterfront rentals Near North Side
- Townhouse rentals Near North Side
- Pet-friendly rentals Near North Side
- Loft rentals Near North Side
- House rentals Near North Side
- Rentals with an EV charger Near North Side
- Rentals with a hot tub Near North Side
- Rentals with a washing machine and dryer Near North Side
- Rentals with outdoor seating Near North Side
- Serviced apartment rentals Near North Side
- Rentals with beach access Near North Side
- Rentals with an accessible-height bed Near North Side
- Rentals with pools Near North Side
- Apartment rentals Chicago
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The Beverly Country Club
- Raging Waves Waterpark
- The 606




