Vacation Rentals in Chicago City Hall, IL: Compare 10+ Sites & Save

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2169 Best Vacation Rentals in Chicago City Hall (Starting from $87)

Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop
Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop
Apartment
Chicago, IL, USA
0.3k from Chicago City Hall center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals

10 Bedrooms25 Guests
8.7

Fabulous

42 reviews

$854
Average price / night
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Blueground | The Loop, AC, w/d, nr Willis Tower
Blueground | The Loop, AC, w/d, nr Willis Tower
Apartment
Chicago, IL, 60606, United States
0.2k from Chicago City Hall center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$131
Average price / night
Check Availability
Loop 1BR w Gym Pool nr Financial District CHI-232
Loop 1BR w Gym Pool nr Financial District CHI-232
Apartment
Chicago, IL, USA
0.3k from Chicago City Hall center

Wellness Facilities, Tv, Business Services, Barbecue/Outdoor Cooking, Security/Safety, Entertainment, Guest Services

1 Bedroom2 Guests
New to Booking
$248
Average price / night
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Blueground | The Loop, elevator, nr Willis Tower
Blueground | The Loop, elevator, nr Willis Tower
Apartment
Chicago, IL, 60606, United States
0.2k from Chicago City Hall center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$123
Average price / night
Check Availability
Loop 1BR w Gym Pool WD nr Financial District CHI-238
Loop 1BR w Gym Pool WD nr Financial District CHI-238
Apartment
Chicago, IL, USA
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$274
Average price / night
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Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop
Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop
Apartment
IL, USA
0.3k from Chicago City Hall center

Apartments, Luxury, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering

13 Bedrooms27 Guests
8.3

Very Good

30 reviews

$319
Average price / night
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Loop 1BR w Gym Pool Lounge 1 block from L CHI-599
Loop 1BR w Gym Pool Lounge 1 block from L CHI-599
Apartment
Chicago, IL, USA
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$111
Average price / night
Check Availability
Loop 1BR w gym pool lounge 1 block from L CHI-671
Loop 1BR w gym pool lounge 1 block from L CHI-671
Apartment
Chicago, IL, USA
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$218
Average price / night
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Loop 1BR w gym pool lounge 1 block from L CHI-700
Loop 1BR w gym pool lounge 1 block from L CHI-700
Apartment
Chicago, IL, USA
0.3k from Chicago City Hall center

Guest Services, Air Conditioner, Security/Safety, Entertainment, Internet, Tv, Pet Friendly

1 Bedroom2 Guests
New to Booking
$87
Average price / night
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Loop 1BR w Pool Gym nr the L Riverwalk CHI-242
Loop 1BR w Pool Gym nr the L Riverwalk CHI-242
Apartment
Chicago, IL, USA
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$258
Average price / night
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Blueground | The Loop, pool & gym, nr Willis
Blueground | The Loop, pool & gym, nr Willis
Apartment
Chicago, IL, 60606, United States
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$156
Average price / night
Check Availability
Premier Penthouses and Apartment with Captivating Views of Millennium Park
Premier Penthouses and Apartment with Captivating Views of Millennium Park
Apartment
Chicago, IL, USA
0.6k from Chicago City Hall center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Self-catering

9 Bedrooms21 Guests
9.0

Fabulous

3 reviews

$2015
Average price / night
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Blueground | The Loop, pool & AC, nr Willis Tower
Blueground | The Loop, pool & AC, nr Willis Tower
Apartment
Chicago, IL, 60606, United States
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$157
Average price / night
Check Availability
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Apartment
Chicago, IL, USA
0.6k from Chicago City Hall center

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

38 Bedrooms14 Guests
7.5

Good

461 reviews

$773
Average price / night
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Loop 1BR w Gym Roof nr Millennium Park CHI-387
Loop 1BR w Gym Roof nr Millennium Park CHI-387
Apartment
Chicago, IL, USA
0.6k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$148
Average price / night
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Luxury High Rise Retreat in the Sky!
Luxury High Rise Retreat in the Sky!
Apartment
Chicago, IL, 60606, United States
0.3k from Chicago City Hall center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

1 Bedroom4 Guests
New to Booking
$192
Average price / night
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2BR Bright & Cozy Apartment - Hubbard 2
2BR Bright & Cozy Apartment - Hubbard 2
Apartment
Chicago, IL, USA
0.7k from Chicago City Hall center

Internet, Fireplace/Heating, Air Conditioner, Security/Safety, Guest Services, Pet Friendly, Child Friendly

2 Bedrooms4 Guests
1.0

Review score

2 reviews

$471
Average price / night
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Blueground | The Loop, pool & gym, nr Willis Tower
Blueground | The Loop, pool & gym, nr Willis Tower
Apartment
Chicago, IL, 60606, United States
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$150
Average price / night
Check Availability
Blueground | Chicago Loop, rooftop, nr Millennium Park
Blueground | Chicago Loop, rooftop, nr Millennium Park
Apartment
Chicago, IL, 60606, United States
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$162
Average price / night
Check Availability
Bright Loop Studio w/ Pool, Gym, nr. Theatre District, by Blueground
Bright Loop Studio w/ Pool, Gym, nr. Theatre District, by Blueground
Apartment
Chicago, IL, 60606, United States
0.3k from Chicago City Hall center

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

1 Bedroom2 Guests
New to Booking
$166
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 Chicago City Hall.

Where to stay in Chicago City Hall? Best neighborhoods & areas

Chicago City Hall Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2169 verified vacation rentals in Chicago City Hall. 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 Chicago City Hall vary depending on the season, property size, and location. Rates typically start from around $87 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 Chicago City Hall 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 Chicago City Hall welcome pets. Currently, 48 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 Chicago City Hall often include amenities such as Fireplace/Heating, Wellness Facilities, and Accessibility. 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.