Book this, not that: Get the most value from your hotel points in Chicago

Chicago is one of the most renowned cities in the U.S. and offers a wondrous array of museums, shopping districts, beaches and history.

Its hotels showcase Chicago culture well. Some properties reflect the industrial hustle and bustle of the city in the late 19th and early 20th centuries when it hosted two world's fairs. Meanwhile, other properties offer more modern additions to the Windy City’s hotel portfolio.

As a result, narrowing down a hotel to stay in can be difficult. When there are many excellent hotels in a stunning city, how can you choose one? Especially when using points and miles, since some properties that seem nice may be a poor redemption.

To spend less time worrying about your Chicago hotel stay and more time finding the best deep-dish pizza, let's look at the Chicago hotels we like — and the ones you can skip.

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Book this: The Ritz-Carlton, Chicago

Chicago is home to a wide array of four- and five-star Marriott properties downtown and in the nearby River North neighborhood. However, it's Marriott’s most renowned chain, Ritz-Carlton, that offers some of the best redemptions for your points.

Stationed right on the Magnificent Mile in the heart of Chicago’s shopping district, The Ritz-Carlton, Chicago offers four restaurant and bar options, a club lounge and a luxurious spa. Rooms have the classic Ritz-Carlton charm but with a modern look.

Rooms are typically priced anywhere from 45,000 to 60,000 Marriott Bonvoy points per night, including Christmas night for just 46,000 points. The cash rate for the same room on Dec. 25 is $539, making each Marriott point worth 1.17 cents. TPG currently values Marriott points at 0.84 cents each, making this redemption at the Ritz an incredible deal.

Related: The award traveler’s guide to Marriott Bonvoy

Skip that: W Chicago — City Center

Although Marriott offers two W properties in the Midwest’s largest city, the W Chicago — City Center is not usually worth redeeming your points for.

Spending only 30,000 points for a night at Marriott’s modern and hip luxury brand may seem like an excellent use of hotel points at first. However, spending cash here is even better. During the Christmas holidays, you can book the W City Center for as little as $152 per night.

In addition, with mediocre reviews and small rooms, the hotel seems to fall below the standard of most W hotels in the Marriott system. For moderately more points, you can have a significantly better stay and a much better redemption at the Ritz-Carlton or one of Marriott’s Autograph, Design or Luxury Collection hotels, like The Gwen.

Related: Should you use points or cash to book hotels?

Book this: Chicago Athletic Association

If you’re looking for an excellent Hyatt redemption in a historical Chicago building, look no further than the Chicago Athletic Association.

The property is housed in a former private athletic club. The building opened at the height of the 1893 World’s Columbian Exposition for one of Chicago’s first football teams. Nowadays, the Hyatt property offers a late 19th-century grandeur combined with Midwestern charm and rooms styled in a midcentury modern aesthetic.

It also has multiple food and beverage options (including an on-site Shake Shack), a rooftop bar and a bocce ball court.

World of Hyatt redemptions are between 12,000 and 18,000 points per night, depending on when you stay. Cash rates at the property can vary widely from $200 a night around Thanksgiving to nearly $750 during summer weekends.

When the cash price is over $300, the Chicago Athletic Association is an excellent World of Hyatt redemption, and Hyatt points can be worth more than 4 cents each at the property’s highest cash rates.

Related: Here’s how to quickly stock up on Hyatt points for your next vacation

Skip that: The Drake

Unlike Marriott and Hyatt, Hilton does not offer many four- or five-star properties in Chicago. As a result, your selection is limited to a few hotels with poor points redemptions.

One such example is The Drake. It offers a similar level of history as the Chicago Athletic Association. However, the rooms show their age, with decor and bedding that looks stiff and ancient, despite bathrooms and a lobby that look oppositely exquisite.

In addition, redemptions have a bit of a range — between 35,000 Hilton Honors points during off-peak winter stays that have a cash rate of $140 and 70,000 points during summer stays that can cost $362. For the superstitious, the hotel has rumors of being haunted.

Related: 7 ways to redeem points with the Hilton Honors program

Book this: Kimpton Hotel Monaco Chicago

Like Hilton, IHG offers only a couple of high-end properties in Chicago. However, redemptions at IHG’s top Chicago hotels generally offer a better bang for your buck than Hilton’s properties.

One of our favorite IHG One Rewards redemptions is at Kimpton Hotel Monaco Chicago, which is recently renovated and at a prime location overlooking the Chicago River and downtown (aka the Loop). The Kimpton offers a stellar seafood restaurant, modern rooms and suites, and in-room spa treatments.

Points redemptions generally range from 30,000 to 80,000 points per night, depending on when you travel. We’ve found that most redemptions generally get 0.6 to 0.8 cents apiece for your IHG points, which is slightly above TPG’s valuation of 0.5 cents.

Related: The award travelers guide to IHG One Rewards

Skip that: Crowne Plaza Chicago West Loop

Compared to other top properties that IHG offers, the Crowne Plaza Chicago West Loop is not in the best location. It's technically in the posh West Loop neighborhood. However, it's a long walk from the neighborhood's famous restaurants and bars and located right next to the Kennedy Expressway.

The Crowne Plaza's outdated rooms and bleak architecture stand out in a city known for its array of stellar skyscrapers. Redemptions provide slightly better value than the 0.5 cents per point that TPG values IHG points at. However, your points can be spent on a nicer property elsewhere in the city.

Related: What is IHG One Rewards elite status worth in 2022?

Bottom line

Chicago has an excellent variety of hotels, some with unique Midwestern charm and Windy City history and others with exquisite modern hospitality.

Marriott's and Hyatt’s hotel programs lead the way for the number of properties you can choose from, although IHG and Hilton have a couple of hotels in prime locations as well.

Bookmark this article and refer to it the next time your travels take you to the Midwest's largest city. It might just save you hours of planning.

Additional reporting by Andrew Kunesh.