Chicago hotel deals are often tough to come by during the busy season, but we have two for you right here.
Chicago’s Swissotel is among the city’s most iconic buildings and a regular standout on its popular riverboat architecture tours. This Travelzoo deal puts you in the iconic hotel for between $109 and $169 per night, depending on when you travel. Through the fall season, the rate is $169 per night, a savings of nearly 50 percent of the normal price for a stay at Swissotel. There’s no better hotel to experience Chicago’s famed riverwalk — the boat tours, as well as many of the city’s top restaurants and museums, are located within walking distance or a quick Uber from the property.
On top of its central location in the heart of Chicago, Swissotel offers amenities you’re generally more likely to find at a luxury beach resort. The $20 daily resort fee covers fitness classes with a smoothie, morning coffee and tea, and fast WiFi throughout the hotel. The fitness center is on the hotel’s 43rd floor and offers incredible views of the skyline and city below.
Photo: Swissotel
Book now for your chance to stay in an iconic Chicago property at a budget rate. And if you change your mind and decide not to travel, Travelzoo will refund your purchase in its entirety. Chicago is best in autumn when the season’s colors drape the city parks. Don’t miss out.
Price:$109 to $169 per night
Stay in a Wrigleyville ‘friends’ unit’ with your entire crew for just $570
Photo: Booking.com
Wrigleyville is as lively as it is historic, and is a must-do for any first-time visitor to Chicago. Whether you’re attending a Cubs game or just want to check out the nightlife, dining, and social scene in one of America’s most beloved neighborhoods, this five-bedroom ‘friends’ unit’ is the best place to base your visit — it’s in the Lakeview district, near Wrigley Field and Montrose Beach.
This ‘friends unit’ is essentially a cross between an Airbnb and a hotel — you get the best of both worlds, without sacrificing location or amenities. There’s a kitchen and parking, as well as five bedrooms and the ability to sleep your entire crew for a super cheap rate. Plus, you can all hang out and pregame on the terrace. This unit is also great for families looking to stay close to the Wrigleyville action while maintaining many of the comforts of home. It’s not a traditional hotel, but this offering is one of the best Chicago hotel deals this fall. 
Price: $571 per night
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We hope you love the spaces and stays we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.