Chicago is one of my favorite cities to visit during autumn. Some of the tourist crush has subsided and the city is famous for enjoying a rather temperate autumn with warm weather sometimes lingering through October. Hotels also come down off their summer peaks during autumn, and in spite of the city being a thoroughly in-demand lodging market, there are some picks to be had on good rates and value-adds here and there.

Park it with Virgin Hotels

Known for brands from records to airlines, cola and beauty products, Virgin Hotels is the British brand giant’s first foray into brick-and-mortar hospitality, and it’s done with the essence of Cool Britannia. Rooms, rather “Chambers” come equipped with mini Smeg fridges and separate sleeping and dressing areas. Elsewhere in the hotel, there are chic dining and nightlife spots, and the hotel even has an app that will dial in to room controls, television and even hotel staff should a request arise.

For weekenders arriving by car this fall, the hotel is offering a room rate that includes valet parking at a discount. Arriving on your own schedule, and not the hotel’s? They let you do that too, with flexible check-in/out times. A spot check of rates for this upcoming weekend found the package available from $389 per night plus tax.

Head “Upstairs at the Gwen” with an upgrade, dining credit, and more

The Gwen, a Luxury Collection Hotel, opened last fall and a year later is offering packages that showcase their Lobby Bar, Circa Restaurant and Lounge, and Upstairs at the Gwen, which features a lovely outdoor terrace. The Taste of the Gwen Package includes a guaranteed table at Upstairs at the Gwen, where guests can enjoy craft cocktails and small plate nibbles with a $50 dining credit per stay, a complimentary room upgrade at the time of booking, and welcome bubbles on arrival. A two-night stay is required, a spot check of rates for early October found nightly rates from $249 per night plus tax.

Get an Old Chicago vibe, and breakfast with a view, at LondonHouse

LondonHouse Chicago, part of Curio, a collection by Hilton is another newcomer to Chicago that opened this year. Repurposed from a landmark 1920’s office tower housing an insurance company, the hotel features a restaurant on the 21st floor and an outdoor terrace on the 22nd, pouring cocktails such as the Roaring Twenties—strawberry and jasmine tea preserve topped with champagne. The building sits right on the Chicago River and the rooftop terrace has some spectacular views.

This fall, guests booking the Breakfast and Wi-Fi rate (about $30 more than the prevailing rate at last check) will get buffet breakfast for two each morning (kids 5 and under eat free with adults) as well as premium in-room Wi-Fi. 

Whether you’re visiting the Windy City as an urban escape, for a museum or theatre weekend, or just to hole up in a nice hotel room with your electronics turned off, autumn is a great time to enjoy some good value in the Heartland.

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