8624+ Hotel & Resort Deals in Chicago |
  1. USA
  2. Illinois
  3. Chicago

Chicago Hotels, Resorts, and Rentals

About Chicago Vacation Rentals

There are more than 8624 places to stay in 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 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 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 Chicago. Places to stay near Chicago are 739.7 ft² on average, with prices averaging $394 a night.

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

Show more
Show less

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

Type Count
Holiday Apartments 5488
Vacation Homes 1527
B&B 91
Hostels 30
Villas 12
Cottages 5
Others 4
Cabin Rentals 2

Use these Quick Filters to Find a Vacation Rental in Chicago

★ Pro Tip: Hotala 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 Chicago.

Weather in Chicago, IL

View the weather forecast for Chicago before booking your 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

Stay Near Chicago's Top Attractions

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


Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Six Flags Great America
University of Chicago
Brookfield Zoo
Northwestern University

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


Chicago 7,560 Properties
Central Chicago 1,879 Properties
Downtown Chicago 1,695 Properties
West Side 798 Properties
Near North Side 764 Properties
The Loop 728 Properties
North Side 676 Properties
River North 429 Properties
South Side 404 Properties
South Loop 397 Properties
Far North Side 390 Properties
Near South Side 385 Properties

Complexes around Chicago, IL


Wells Apartments St Chicago 132 Properties
Town 17 Properties
South Loop Grant Park 29 Properties
Kasa River North 25 Properties
Wrigley 35 Properties
Lakeview 18 Properties
Accommodation Schaumburg 26 Properties
Transit Dt 14 Properties
Naperville Inn 10 Properties
Gold Coast Doorman Blocks 9 Properties
Lofts 14 Properties
Belmont 7 Properties
Mccormick Place 5 Properties
Sonder South Wabash 11 Properties
District Block 10 Properties
See More Complexes

Frequently Asked Questions About Chicago?

What are the top hotels or resorts in Chicago?

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

How many vacation rentals have private pools in Chicago?

There are 93 accommodation options with private pools in or near Chicago. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

Which hotel or resort in Chicago is best for families?

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

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 8624 in the 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 Chicago.

Nearby Neighborhood (16) 
Neighborhood Property Count
Downtown Chicago Hotel & Resort Deals in Chicago, Illinois 1695
Near North Side Hotel & Resort Deals in Chicago, Illinois 764
The Loop Hotel & Resort Deals in Chicago, Illinois 728
River North Hotel & Resort Deals in Chicago, Illinois 429
South Loop Hotel & Resort Deals in Chicago, Illinois 397
Near South Side Hotel & Resort Deals in Chicago, Illinois 385
Lakeview Hotel & Resort Deals in Chicago, Illinois 293
West Loop Hotel & Resort Deals in Chicago, Illinois 203
Lincoln Park Hotel & Resort Deals in Chicago, Illinois 159
Hyde Park Hotel & Resort Deals in Chicago, Illinois 123
Logan Square Hotel & Resort Deals in Chicago, Illinois 71
Rogers Park Hotel & Resort Deals in Chicago, Illinois 68
O'Hare Hotel & Resort Deals in Chicago, Illinois 60
Edgewater Hotel & Resort Deals in Chicago, Illinois 56
Wrigleyville Hotel & Resort Deals in Chicago, Illinois 49
Wicker Park Hotel & Resort Deals in Chicago, Illinois 47

People Also Ask

There are 746 hotels in Chicago 142 resorts, and 7029 rentals

Recently Booked Hotels, Resorts, or Rentals in Chicago