Vacation Rentals in Streeterville, IL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  Illinois

  5.  Chicago
  6.  Streeterville

Refine your search

Price per night

Amenity Filter

Rating

2092 Best Vacation Rentals in Streeterville (Starting from $84)

Sonder by Marriott Bonvoy Onterie Apartments Magnificent Mile
Sonder by Marriott Bonvoy Onterie Apartments Magnificent Mile
Apartment
Chicago, IL, USA
0.0k from Streeterville center

Apartments, Cheap, Accommodations, Serviced apartments, Lodgings, Places to stay, Self-catering

101 Bedrooms17 Guests
8.4

Very Good

44 reviews

$209
Average price / night
Check Availability
Blueground | Streeterville, pool & gym, nr pier
Blueground | Streeterville, pool & gym, nr pier
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$201
Average price / night
Check Availability
Streeterville 1BR w Gym Pool nr Navy Pier CHI-447
Streeterville 1BR w Gym Pool nr Navy Pier CHI-447
Apartment
Chicago, IL, USA
0.1k from Streeterville center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom2 Guests
New to Booking
$141
Average price / night
Check Availability
ENVITAE 3BR Downtown Luxurious Suite Views & Pool
ENVITAE 3BR Downtown Luxurious Suite Views & Pool
Apartment
Chicago, IL, USA
0.4k from Streeterville center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

3 Bedrooms7 Guests
9.0

Fabulous

20 reviews

$1703
Average price / night
Check Availability
Streeterville 1br w pool roof gym nr lakefront CHI-827
Streeterville 1br w pool roof gym nr lakefront CHI-827
Apartment
Chicago, IL, USA
0.6k from Streeterville center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$184
Average price / night
Check Availability
Elegant Streeterville Studio w/ Gym, Pool, near Navy Pier, by Blueground
Elegant Streeterville Studio w/ Gym, Pool, near Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$200
Average price / night
Check Availability
Streeterville 1BR w Lake Views Pool Deck Gym CHI-183
Streeterville 1BR w Lake Views Pool Deck Gym CHI-183
Apartment
Chicago, IL, USA
0.6k from Streeterville center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom2 Guests
New to Booking
$167
Average price / night
Check Availability
Tasteful Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground
Tasteful Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$204
Average price / night
Check Availability
Gold Coast 2BR w Gym Roof nr Water Tower CHI-389
Gold Coast 2BR w Gym Roof nr Water Tower CHI-389
Apartment
Chicago, IL, USA
0.7k from Streeterville center

Security/Safety, Internet, Tv, Air Conditioner, Guest Services, Wellness Facilities, Fireplace/Heating

2 Bedrooms4 Guests
New to Booking
$84
Average price / night
Check Availability
Beautiful Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground
Beautiful Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$97
Average price / night
Check Availability
Luxurious Haven in the Heart of Chicago! [32 Day+]
Luxurious Haven in the Heart of Chicago! [32 Day+]
Apartment
Chicago, IL, USA
0.9k from Streeterville center

Balcony/Terrace, Parking, Wheelchair Accessible, Pool, Kitchen, Internet, Air Conditioner

2 Bedrooms4 Guests
New to Booking
$191
Average price / night
Check Availability
Lovely Streeterville Studio w/ Gym, Pool, near Navy Pier, by Blueground
Lovely Streeterville Studio w/ Gym, Pool, near Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$111
Average price / night
Check Availability
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
Apartment
Chicago, IL, USA
0.9k from Streeterville center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Hot tubs

9 Bedrooms24 Guests
9.2

Superb

28 reviews

$1103
Average price / night
Check Availability
Splendid Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground
Splendid Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$201
Average price / night
Check Availability
River N 1BR w Gym WD nr Magnificent Mile CHI-162
River N 1BR w Gym WD nr Magnificent Mile CHI-162
Apartment
Chicago, IL, USA
0.9k from Streeterville center

Accessibility, Barbecue/Outdoor Cooking, Entertainment, Security/Safety, Business Services, Air Conditioner, Tv

1 Bedroom2 Guests
New to Booking
$148
Average price / night
Check Availability
Amazing Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, by Blueground
Amazing Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$187
Average price / night
Check Availability
River N 2BR w Gym WD nr Magnificent Mile CHI-164
River N 2BR w Gym WD nr Magnificent Mile CHI-164
Apartment
Chicago, IL, USA
0.9k from Streeterville center

Tv, Business Services, Barbecue/Outdoor Cooking, Accessibility, Internet, Wellness Facilities, Security/Safety

2 Bedrooms4 Guests
New to Booking
$352
Average price / night
Check Availability
Luxe Streeterville Studio w/ Gym, Pool, walk to Navy Pier, by Blueground
Luxe Streeterville Studio w/ Gym, Pool, walk to Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$115
Average price / night
Check Availability
River N 1BR w Gym WD nr Mag Mile CHI-86
River N 1BR w Gym WD nr Mag Mile CHI-86
Apartment
Streeterville, Chicago, Illinois, USA
0.9k from Streeterville center

Accessibility, Barbecue/Outdoor Cooking, Entertainment, Security/Safety, Business Services, Air Conditioner, Tv

1 Bedroom2 Guests
New to Booking
$169
Average price / night
Check Availability
Modern Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, by Blueground
Modern Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$211
Average price / night
Check Availability
River N 1BR w Gym WD nr Mag Mile CHI-85
River N 1BR w Gym WD nr Mag Mile CHI-85
Apartment
Chicago, IL, USA
0.9k from Streeterville center

Air Conditioner, Tv, Internet, Accessibility, Business Services, Guest Services, Fireplace/Heating

1 Bedroom2 Guests
New to Booking
$250
Average price / night
Check Availability
Ideal Streeterville Studio w/ Gym, Pool, walk to Navy Pier, by Blueground
Ideal Streeterville Studio w/ Gym, Pool, walk to Navy Pier, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$115
Average price / night
Check Availability
Upscale Streeterville Studio w/ Dog Run & Deck, near Park, by Blueground
Upscale Streeterville Studio w/ Dog Run & Deck, near Park, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$206
Average price / night
Check Availability
Modern Streeterville Studio w/ Pool & Dog Run, near Beach, by Blueground
Modern Streeterville Studio w/ Pool & Dog Run, near Beach, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$121
Average price / night
Check Availability
Trendy Streeterville Studio w/ Deck & Pool, close to Beach, by Blueground
Trendy Streeterville Studio w/ Deck & Pool, close to Beach, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$99
Average price / night
Check Availability
Deluxe Streeterville 1BR w/ Gym & Pool, close to Beach, by Blueground
Deluxe Streeterville 1BR w/ Gym & Pool, close to Beach, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$222
Average price / night
Check Availability
Sleek Streeterville Studio w/ Pool & Gym, near Park, by Blueground
Sleek Streeterville Studio w/ Pool & Gym, near Park, by Blueground
Apartment
Chicago, IL, 60611, United States
0.1k from Streeterville center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$149
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Streeterville.

Where to stay in Streeterville? Best neighborhoods & areas

Stay Near Streeterville's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Streeterville Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2092 verified vacation rentals in Streeterville. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Streeterville vary depending on the season, property size, and location. Rates typically start from around $84 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Streeterville include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Streeterville welcome pets. Currently, 60 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Streeterville often include amenities such as Accessibility, Wellness Facilities, and Fireplace/Heating. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.