Trips to Chicago

Plan Your Next Trip to Chicago and explore unforgettable sights, local flavors, and exciting experiences.

Find the Best Accommodations for Your Chicago Trip

Smartours makes it easy to discover stays that match your style, budget, and location.

  • Hotels
  • Villas
  • Cabins
  • apartments
  • Cottages
  • Resorts
  • Ski chalets
6.6 (33 Reviews)
Hotel
Luxe Romantic Suites
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
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10 (19 Reviews)
Hotel
Sinclair Suites
  • Air Conditioner
  • Parking
  • Security/Safety
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3.7 (7 Reviews)
Hotel
Americas Best Value Inn Waukegan
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
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10 (5 Reviews)
Apartment
The Oak Park Loft
  • Parking
  • Balcony/Terrace
  • Security/Safety
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10 (1 Review)
House
Riverfront Cottage
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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9.7 (3 Reviews)
House
Cottingham Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
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9.4 (94 Reviews)
Cottage
A Diamond in the Rough
  • Air Conditioner
  • Parking
  • Pet Friendly
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8 (231 Reviews)
Resort
Eaglewood Resort & Spa
  • Air Conditioner
  • Parking
  • Pet Friendly
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8 (117 Reviews)
Resort
Lincolnshire Marriott Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
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Top Rated Activities & Tours in Chicago

Chicago River Architecture: History and Sightseeing Cruise
Chicago River Architecture: History and Sightseeing Cruise
10
Excellent
16032 Reviews
5 star rating Recommendation
From
US $39 Per Person
Reserve
Chicago Architecture River Cruise
Chicago Architecture River Cruise
10
Excellent
16060 Reviews
5 star rating Recommendation
From
US $39 Per Person
Reserve
Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
10
Excellent
2064 Reviews
5 star rating Recommendation
From
US $84 Per Person
Reserve
Chicago Architecture Center River Cruise aboard First Lady
Chicago Architecture Center River Cruise aboard First Lady
10
Excellent
5832 Reviews
5 star rating Recommendation
From
US $57 Per Person
Reserve
See More Activities & Tours in Chicago

Why Book Your Trip to Chicago with Smartours?

Here’s why smart travelers plan travel with Smartours

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Smarter Stays

Hotels, villas, and vacation rentals selected for comfort, location and value – giving you the ideal base for your adventures.
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Smarter Itineraries

AI-powered trip plans that bundle accommodations, transport, and activities into flexible packages you can tailor to your style and budget.
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Smarter Exploration

Self-guided itineraries filled with local insights, hidden gems, and authentic experiences beyond the typical tourist trail.

How to Book Your Stay in Chicago?

What’s the Smartours booking process?

Our platform connects you to a curated selection of hotels, villas, and unique stays in Chicago. Once you’ve found your ideal property, you’ll be redirected to our trusted booking partner to complete your reservation securely and with confidence.

Booking Steps

01

Search Stays

Use Smartours filters to find accommodations that match your style, location preferences, and budget.
02

View Details

Click on a listing to see photos, amenities, reviews, and pricing.
03

Book Securely

Follow the link to finalize your reservation directly with our verified booking partner.
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Indoor Features

  • Fully equipped kitchens or kitchenettes
  • Comfortable living areas with smart TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-room coffee and tea facilities
  • Premium bedding for restful nights
  • Modern bathrooms with walk-in showers or soaking tubs

Outdoor Amenities

  • Balconies, terraces, or rooftop lounges with scenic views
  • Swimming pools, either private or shared
  • Outdoor dining spaces with BBQ or grill access
  • Gardens or courtyards for relaxing downtime
  • On-site parking or easy transport access
  • Proximity to key attractions, markets, or nature trails

Other Places to Stay in Chicago

3 (193 Reviews)
House
Homan Square
  • Parking
  • Child Friendly
  • Internet
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10 (510 Reviews)
Bed & Breakfast
The Sono Chicago
  • Air Conditioner
  • Parking
  • TV
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Seasonal Weather in Chicago

What’s the weather like in Chicago throughout the year?

Chicago’s climate varies by region, but most areas enjoy mild to warm weather year-round. Coastal cities benefit from ocean breezes, while inland areas and the desert see greater temperature swings between day and night.

Wednesday May 20

Chicago, Illinois

Wed
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10.2°C
Thu
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11.8°C
Fri
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11.8°C
Sat
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12.8°C
Sun
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18.9°C
Mon
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17.8°C
Tue
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19.6°C

Frequently Asked Questions

What are the top vacation rentals in Chicago?
How many vacation rentals have private pools in Chicago?

There are 339 vacation rentals with private pools near Chicago. Top-rated homes that have access to a swimming pool include:

Which vacation homes in Chicago are best for families?

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

How many vacation rentals are available in Chicago?

Currently, the total number of properties listed in 2026 is over 12417 in the Chicago area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chicago.

More Accommodations You May Like for Trips to Chicago

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