
Apartment holiday rentals in Near North Side
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Top-rated apartment rentals in Near North Side
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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

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 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 fireplace is not operational.

3-bedroom exposed brick in Chicago's Wicker Park
Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

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.

RockStar Pad W3A BoysTown/Wrigley Field/Parking
HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Spacious 4 Bedroom Condo
Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

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.

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

Sunny Apartment Just 2 Blocks from Wrigley and Boystown

Christmas in the City- Holiday Duplex in Lakeview

Spacious 3BR • Great for Groups • Fast WiFi • Pets
The Penthouse Gallery at OHC - No Cleaning Fee!

Lincoln Square Gem!

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

Tri-Taylor/Medical Dist. near West Loop

Near Lake Michigan & Wrigley Field
Pet-friendly apartment rentals

Chic and Charming Vintage Condominium in Lincoln Park

Cozy Lincoln Park Condo near the lake.

Luxuriously bright 3-bedroom condo: The Treehouse

Picture Perfect 3Bed Steps from Train and FLW

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Spacious 5-BR Apt next to transit Free Parking

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

Large Remodeled Home in Lincoln Park, Sleeps 12!
Apartment rentals with a pool

Location! LUX 2b/2b Condo Amazing Views/Amenities

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

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

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 | £100 | £99 | £105 | £124 | £129 | £133 | £133 | £133 | £109 | £114 | £106 | £109 |
| 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 £15 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 outdoor seating Near North Side
- Rentals with a fireplace Near North Side
- Rentals with an accessible-height bed Near North Side
- Rentals with beach access Near North Side
- Waterfront rentals Near North Side
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- Rentals with a firepit Near North Side
- House rentals Near North Side
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- Serviced apartment rentals Near North Side
- Rentals with a patio Near North Side
- Rentals with a hot tub Near North Side
- Pet-friendly rentals Near North Side
- Rentals with lake access Near North Side
- Family-friendly rentals Near North Side
- Rentals with breakfast Near North Side
- Rentals with a cinema Near North Side
- Townhouse rentals Near North Side
- Rentals with an EV charger Near North Side
- Rentals with a sauna Near North Side
- Rentals with pools Near North Side
- Fitness-friendly rentals Near North Side
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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
- Brookfield Zoo
- Willis Tower
- Museum of Science and Industry
- Illinois Beach State Park
- The Beverly Country Club
- Washington Park Zoo
- The 606
- Raging Waves Waterpark




