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

Rare 1BR Lincoln Park Apt, close to everything!
Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.

Spectacular Penthouse Corner 2BR in Streeterville
Stunning 1,200 square foot top-floor corner penthouse with oversize windows, an open layout, and dramatic city and lake views in multiple directions. This bright and modern two bedroom, one bathroom apartment is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360° views of the skyline and the lake. This is the best location in the city!

Kasa | Explore the Neighborhood-Mag Mile | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations steps from world-class shopping and restaurants, Oak St. beach, and public transportation (L trains, express bus). Includes A/C, washer-dryer, super-fast wi-fi, smart TV, and workspace. Hourly rate garage parking next door. Note: Guests must walk up one flight of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

Urban Chic Apartment by the Magnificent Mile
Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely, if ever, in the bedrooms.

2br/2ba, A+ location by Mag mile, views & spacious
Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. I'm happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/helpful host, Flexible luggage policy) Please see Airbnb listing 12323073 for additional reviews of this apartment.

Peaceful River West, free parking
This Apt can be rented separately or together with Comfy River West Apt. https://abnb.me/aoJ0F64vDY This one on the the 2nd floor and one directly above on the 3rd floor. Together they will sleep 8 guest. This beautiful 2BR, 1 BA has all new furniture, all new appliances, counter tops, vanity, mirrors. Free parking in a gated lot, Level 2 EV charging available for electric cars. Shared patio/gardens and grill. Fully stocked kitchen, private washer & dryer.

Historic Old Town Flat - Minutes from Downtown!
Built in 1886, our "Boland House" offers guests a rare chance to stay in an architecturally significant residence on a beautiful tree-lined street in Historic Old Town district! The original owner was chief of plasterwork projects for the "White City's" 1893 World's Columbian Exposition - combined with modern day conveniences. If you've always wanted to stay in an authentic Chicago Victorian brownstone, you've found it!

Modern 3BR with Private Rooftop & Free Parking
A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Elegant Suite in Gold Coast
Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of May 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours***

Coach House in Historic Old Town Chicago
Our coach house is the perfect place for your stay in Chicago. Located walking distance from restaurants, Lake Michigan, the beach and public transportation, it will make your stay in Chicago easy and eventful. We can tell you everything you need to know about the best places in the city. You'll feel right at home here on your Chicago adventure.
Popular amenities for Near North Side apartment rentals
Weekly apartment rentals

Condo Near Downtown Chicago

River North | Rooftop With In & Out Parking | 3

Modern Chicago Getaway – Near Downtown

Fulton House #1 (2bd/ 1ba)

Downtown Chicago Retreat 2BD 2BA Views Gym Rooftop

South Loop Studio Hotel (301)

Hancock Lookout|Steps to Beach&Transit, CHI Views

Luxury Designer Penthouse|Private Deck|Gold Coast
Private apartment rentals

51st Floor MagMile Penthouse Views Balcony Pool

Modern River West 2 Bed 2 Bath-Steps to Blue Line

Spacious loft w/ vintage details

Stylish Gold Coast 3BR Apt | Walk to Grocery&Cafes

Svaha - Serene 2BR Oasis in East Village

Loop 2BR w/Lake Views | 10 min to Millennium Park

Sophisticated, 2-BR Condo in Old Town

ChiCasa Wicker Park Paradise
Apartment rentals with a hot tub

Level Junior Two Bedroom Suite | Fulton Market

Luxury 3BD Penthouse – Private Patio+Skyline Views

Skyline Oasis: City & Lake Views

Chic 1 BR w 1 G Parking| W Park Nightlife nearby

Belmont Pleasures - hot tub / arcade gaming room

420 friendly apt with 2 queens,1 full,1 twin bed

Checkerboard Studio, Private Outdoor Hot Tub, Yard

South Loop Suite (Indoor Pool • Fitness Center)
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 | $180 SGD | $200 SGD | $219 SGD | $244 SGD | $316 SGD | $357 SGD | $336 SGD | $310 SGD | $278 SGD | $259 SGD | $226 SGD | $206 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 flat rentals in Near North Side

Total holiday rentals
Explore 1,080 holiday rentals in Near North Side

Nightly prices starting at
Near North Side holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 30,860 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 610 rentals that welcome pets

Holiday rentals with a pool
540 properties feature pools

Rentals with dedicated workspaces
480 properties have a dedicated workspace

Wifi availability
1,060 of Near North Side holiday rentals include wifi access

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

4.7 Average rating
Near North Side stays receive an average rating of 4.7 out of 5 from guests

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 pools Near North Side
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- Rentals with a firepit Near North Side
- Apartment rentals Near North Side
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- Serviced apartment rentals Near North Side
- Loft rentals Near North Side
- Rentals with beach access Near North Side
- Townhouse rentals Near North Side
- Rentals with a washing machine and dryer Near North Side
- Rentals with outdoor seating Near North Side
- Rentals with an EV charger Near North Side
- Pet-friendly rentals Near North Side
- Rentals with breakfast Near North Side
- Rentals with a cinema Near North Side
- Rentals with a hot tub Near North Side
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- House rentals Near North Side
- Flat rentals Chicago
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- University of Chicago




