2381+ Hotel & Resort Deals in Downtown Chicago |
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Downtown Chicago Hotels, Resorts, and Rentals

About Downtown Chicago Vacation Rentals

There are more than 2381 places to stay in Downtown 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 Downtown 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 Downtown 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 Downtown Chicago. Places to stay near Downtown Chicago are 716.94 ft² on average, with prices averaging AU $697 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Downtown 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 Downtown Chicago

Type Count
Holiday Apartments 1420
Vacation Homes 571
Villas 3
Cabin Rentals 2
B&B 1

Use these Quick Filters to Find a Vacation Rental in Downtown Chicago

★ Pro Tip: Hotala.com.au 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 Downtown Chicago.

Weather in Downtown Chicago, IL

View the weather forecast for Downtown Chicago before booking your Downtown 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


Chicago 7,168 Properties
Chicago 4,154 Properties
Central Chicago 1,901 Properties
Near North Side 781 Properties
The Loop 775 Properties
River North 447 Properties
Streeterville 203 Properties
West Loop 197 Properties
Rush and Division 76 Properties
Gold Coast 39 Properties
Killgubbin 37 Properties
West Loop Gate 24 Properties

Frequently Asked Questions About Downtown Chicago?

What are the top hotels or resorts in Downtown Chicago?

You have a lot of choices in or near Downtown Chicago. If you need a hotel in the Downtown 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 Downtown Chicago:

How many vacation rentals have private pools in Downtown Chicago?

There are 56 accommodation options with private pools in or near Downtown Chicago. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

Which hotel or resort in Downtown Chicago is best for families?

If you are looking for a family-friendly hotel, resort, or vacation home in Downtown 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 Downtown Chicago:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 2381 in the Downtown 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 Downtown Chicago.

Nearby Neighborhood (16) 
Neighborhood Property Count
Near North Side Hotel & Resort Deals in Chicago, Illinois 781
The Loop Hotel & Resort Deals in Chicago, Illinois 775
River North Hotel & Resort Deals in Chicago, Illinois 447
South Loop Hotel & Resort Deals in Chicago, Illinois 355
Near South Side Hotel & Resort Deals in Chicago, Illinois 343
Near West Side Hotel & Resort Deals in Chicago, Illinois 334
West Town Hotel & Resort Deals in Chicago, Illinois 280
Streeterville Hotel & Resort Deals in Chicago, Illinois 203
West Loop Hotel & Resort Deals in Chicago, Illinois 197
Lincoln Park Hotel & Resort Deals in Chicago, Illinois 144
University Village / Little Italy Hotel & Resort Deals in Chicago, Illinois 91
Old Town Hotel & Resort Deals in Chicago, Illinois 51
River West Hotel & Resort Deals in Chicago, Illinois 51
Gold Coast Hotel & Resort Deals in Chicago, Illinois 39
Magnificent Mile Hotel & Resort Deals in Chicago, Illinois 4128
Lakeshore East Hotel & Resort Deals in Chicago, Illinois 735

People Also Ask

There are 264 hotels in Downtown Chicago 26 resorts, and 1996 rentals

Recently Booked Hotels, Resorts, or Rentals in Downtown Chicago