Bespoke Usa Travel - Vacation Rentals in Near East Side

Magic Factory Loft 2East 4 Bd/3 Ba Families Groups From US $822
         

10.0 (119 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Internet
3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $271
         

52nd Floor MagMile Penthouse VIEWS Fireplace Pool From US $281
         

51st Floor MagMile Penthouse Views Balcony Pool From US $265
         

Luxury Places to Stay in Near East Side

Over 3628+ Luxury Places to Stay in or Near Near East Side
6 Luxe Apts, Perfect Group Solution, Sleeps 30 From US $3,767
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
: The Wolcott : Modern Elegance at Its Finest From US $3,480
         

Exclusive Group Getaway in Vibrant West Loop From US $3,433
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Iconic Downtown Penthouses Getaway + City Views From US $3,151
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Near East Side

Over 1126+ Top-Rated Vacation Rentals with a Pool in or Near Near East Side
53 Floor MagMile Penthouse Views, Balcony, Pool From US $303
         

53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool From US $608
         

52nd Floor, VIEWS, Pool, Balcony, Pool, Gym From US $221
         

10.0 (61 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym From US $242
         

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool From US $522
         

10.0 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Designer Penthouse West |Pool| Gold Coast From US $516
         

10.0 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Near East Side

Over 1719+ Pet-Friendly Vacation Rentals in or Near Near East Side
Large 4BR/3BA Safe Old Town Location Walk Everywhere From US $809
         

10.0 (73 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
4BR Corporate Suite Central and Modern From US $403
         

10.0 (8 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Luxury House in the heart of Old Town with Parking From US $1,512
         

10.0 (56 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba From US $311
         

10.0 (26 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Loft Collection 703 - Terrace - River North From US $575
         

10.0 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Loft Collection 02 - Terrace - River North From US $569
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury SOHO Styled Two-Level Townhouse - Old Town From US $531
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Near East Side

Over 411+ Large Vacation Homes & Villas in or Near Near East Side
Magic Factory Loft 3East 4 Bd/4 Ba Families Groups From US $1,119
         

10.0 (106 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Lux Apts with Lake Views and Top Amenities From US $1,582
         

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10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10 From US $309
         

New
Apartment
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  • Parking
  • Pet Friendly
Spacious 4-Level/4-Bedroom Townhouse in West Loop From US $935
         

Lovely 4 Bedroom Spot located in Charming Old Town From US $850
         

10.0 (36 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
City Center, River North Condo HUGE 3BR, Patio, Parking(2x) From US $773
         

Wheelchair Accessible Vacation Homes in Near East Side

Over 2390+ Wheelchair Accessible Vacation Homes in or Near Near East Side
Downtown Guild #3 | Mag Mile Gold Coast The Lake! From US $200
         

10.0 (21 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
The Publishing House B&B From US $217
         

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9.8 (188 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba From US $310
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area From US $792
         

53-54 Floor Penthouse From US $609
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Luxury Loft Collection 903 - Terrace - River North From US $591
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic Charm + Modern Comfort for Tourists From US $406
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

Near East Side Varoom and Airbnb Places to Stay Under $200

Over 1522+ Near East Side Varoom and Airbnb Places to Stay Under $200
Spacious & private! Free parking! Great location! From US $147
         

10.0 (31 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern River West 2BR with W&D by Zencity From US $77
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
The Sono Chicago From US $154
         

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10.0 (483 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Spacious loft in the heart of West Town, Noble Square Chicago From US $159
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Stylish 1BR in West Loop From US $180
         

10.0 (10 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Gold Coast Living: Modern Studio Unit From US $176
         

10.0 (4 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
West Loop Living – Bright 1BR From US $159
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Near East Side

Over 2312+ Instantly Bookable Vacation Homes in or Near Near East Side
Twice as Nice: Chic 2BR Stay with Style & Space From US $266
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
1F Chicago's Little italy Graystone nearDowntown From US $243
         

10.0 (168 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Brilliant Downtown Chicago 3-Bedroom Condominium From US $416
         

10.0 (50 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Gorgeous 3BR River North Condo - Free Parking From US $683
         

10.0 (29 Reviews)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
Trendy West Town Flat - 2 bed/1.5 bath with parking From US $273
         

Luxury Modern home minutes from Downtown Chicago From US $469
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Near East Side Vacation Rentals

With more than 3637 Near East Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Near East Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bespokeusatravel Near East Side, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Near East Side. Places to stay near Near East Side are 750.99 ft² on average, with prices averaging $382 a night.

Bespokeusatravel makes it easy and safe to find and compare vacation rentals in Near East Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Near East Side

Type Count
Holiday Apartments 2331
Hotels with Suites 648
Vacation Homes 405
Resorts 25
B&B 6
Hostels 5
Villas 3
Others 2
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Near East Side

Pro Tip: Bespokeusatravel makes it easy to compare the best listings on Bespokeusatravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bespokeusatravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Near East Side.

Weather in Near East Side

View the weather forecast for Near East Side before booking your Near East Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Near East Side, IL