1500+ Hotel & Resort Deals in Heart of Chicago |
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Heart of Chicago Hotels, Resorts, and Rentals

About Heart of Chicago Vacation Rentals

There are more than 1500 places to stay in Heart of Chicago that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Heart of Chicago.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Heart of Chicago, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Heart of Chicago. Places to stay near Heart of Chicago are 780.22 ft² on average, with prices averaging GB £279 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Heart of Chicago with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Heart of Chicago

Type Count
Holiday Apartments 1148
Vacation Homes 121
B&B 9
Villas 3
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Heart of Chicago

★ Pro Tip: Hotala.uk has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Heart of Chicago.

Weather in Heart of Chicago, IL

View the weather forecast for Heart of Chicago before booking your Heart of Chicago 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

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


St Adalbert Church 2,708 Properties
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Canalport Riverwalk Park 1,643 Properties
Lower West Side 909 Properties

Frequently Asked Questions About Heart of Chicago?

What are the top hotels or resorts in Heart of Chicago?

You have a lot of choices in or near Heart of Chicago. If you need a hotel in the Heart of Chicago area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Heart of Chicago:

How many vacation rentals have private pools in Heart of Chicago?

There are 6 accommodation options with private pools in or near Heart of Chicago. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

Which hotel or resort in Heart of Chicago is best for families?

If you are looking for a family-friendly hotel, resort, or vacation home in Heart of Chicago, check out one of the following places to stay as all are highly-rated accommodation choices with excellent reviews for families or groups staying in Heart of Chicago:

How many hotels, resorts, or rentals are available in Heart of Chicago?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 1500 in the Heart of Chicago area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Heart of Chicago.

Nearby Neighborhood (5) 
Neighborhood Property Count
Near West Side Hotel & Resort Deals in Chicago, Illinois 63
University Village / Little Italy Hotel & Resort Deals in Chicago, Illinois 743
Lower West Side Hotel & Resort Deals in Chicago, Illinois 909
Pilsen Hotel & Resort Deals in Chicago, Illinois 3300
McKinley Park Hotel & Resort Deals in Chicago, Illinois 739

People Also Ask

There are 95 hotels in Heart of Chicago and 1272 rentals

Recently Booked Hotels, Resorts, or Rentals in Heart of Chicago