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Chicago is one of the best getaways in the Midwest U.S., especially in the Spring and Fall. My top activity recommendations are to take an architecture river cruise, see a comedy show, and go on a food tour. So I’ve rounded up some cool hotels in Chicago.
Plan The Perfect Trip To Chicago
From historic high-rises and boutique hotels to luxury suites and vintage rooms, I’ve got the perfect hotel for you.
Here are cool hotels in Chicago for your next trip!
Viceroy Chicago
This glamorous mid-century modern hotel is my favorite in the city. Every room has floor-to-ceiling windows with views of the city or Lake Michigan, and you’ll love the luxurious bathrooms. There’s also a rooftop pool, two on-site restaurants, and a fitness center.
Kimpton Gray Hotel
Get ready to fall in love with this modern luxe hotel with historic architecture juxtaposed against contemporary-styled guest rooms. The lobby bar is a refined sanctuary with bookshelves, leather seating, and low lighting. There’s also a Latin restaurant with a high-energy/nightclub vibe on the top floor.
Chicago Athletic Association Hotel
Chicago Athletic Association Hotel
Originally home to an elite men’s club, this building is an architectural gem from the late 1800s. This boutique hotel has seven bars and restaurants, the city’s first Topgolf Swing Suite, and the perfect downtown location. Here, you’ll have an artfully-restored historic stay, along with some of the city’s best rooftop dining.
Nobu Hotel Chicago
If you want a luxurious, perfectly located hotel, the Nobu is for you. You’ll love the on-site restaurant with stunning views of the city skyline, the indoor tranquility pool, floor-to-ceiling windows, minimalistic decor, and the hotel’s location on Restaurant Row.
Pendry Chicago
Set within the iconic 1929 Art Deco Carbide & Carbon Building in Chicago’s Loop neighborhood, Pendry Chicago is a modern-day luxury hotel that pays homage to the past and the present with contemporary, comfortable interiors, signature culinary and cocktail concepts, and inspired gathering spaces.
The Peninsula Chicago
Enjoy having the city at your feet from this incredible pool, rooftop restaurant, and outdoor lounge. This property’s overall atmosphere is artistic, eclectic, and trendy, and every inch of this hotel is Insta-perfect.
The Blackstone, Autograph Collection
The Blackstone, Autograph Collection
Teddy Roosevelt and Al Capone were once guests at this historic “Hotel of Presidents” facing Grant Park. Historic architecture, coffered ceilings, and antique furniture are seamlessly blended with contemporary amenities and colors. You’ll love the pop-up hutch bar in the lobby and the on-site tapas restaurant.
The Langham, Chicago
This hotel occupies the top floors of the famous IBM Building – the last skyscraper built by the renowned Mies van der Rohe. The rooms are mid-century modern with an emphasis on the modern. There’s a health club, spa, two restaurants, a ballroom, and a fine art collection with more than 150 pieces of art.
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What do you think are some cool hotels in Chicago? Share with us in the comments!
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Cool Hotels in Chicago
Frequently Asked Questions
Is Chicago safe for tourists?
I felt very safe every time I’ve visited Chicago. But, as with any destination, you need to take precautions to keep yourself safe. Don’t walk by yourself at night, stay in a secure and well-located hotel or vacation home, use slash-proof, lockable, and RFID-protected bags and purses, and always have a charged cell phone with you.
What is the best month to visit Chicago?
June – August is Chicago’s peak tourism and festival season. Accommodation rates and crowds will be at their highest, so book hotels, Airbnbs, tickets, and tours in advance. These months are peak baseball season, so make sure you check if there are home games when you plan to visit. Home games will make prices and tourist numbers even higher. Average summer temperatures range from the high 50s to the mid-80s, so pack a mix of clothes and be prepared for rain in August.
September and October are beautiful months to visit the city. The foliage will be changing, and the temperatures will be pleasantly cool (you’ll want layers for the mornings and evenings). Accommodation prices and crowds will be on the decline, and the city hosts an incredible Oktoberfest.
Winter is cold and windy with high snow chances, and winter lasts from November well into March (daytime highs are in the low 30s to high 40s, but wind chills can cause temperatures to drop into the negatives). If you’re okay with the cold, then you can score some great hotel deals in these months.
Spring is short and beautiful in Chicago. April and May have daytime temperatures between the high 50s and low 70s, and the city is covered in flowers. Make sure you have rain gear with you during these months. Prices and crowds will be on the rise, especially around Spring Break weeks, but you can still find some great accommodation and airfare deals.
How do tourists get around Chicago?
It’s easy (and very enjoyable!) to walk around Chicago’s neighborhoods. But if you’re going to traverse the town, then you’ll want to use rideshares or the city’s metro lines.
Is Chicago an expensive city?
Chicago is a relatively expensive city to visit, but there are lots of free activities here. To save some money, visit on weekdays and during the shoulder of off-seasons, and eat out for lunch or prep your own meals.
How much is an Uber from O'Hare to downtown Chicago?
Because of Uber’s surge pricing, rideshares from the airport to downtown can range from $35-140 depending on the time of day. Pre-arranged taxis or shuttles can save you money and time when going from the airport to downtown. You can also take CTA trains (Chicago’s public transportation) to downtown for cheap.
Is it easy to drive in Chicago?
Not for visitors. Chicago’s packed streets, ever-changing road rules from hour to hour and day to day, stressful rules-of-the-road, and limited and expensive parking mean visitors should drive as little as possible while visiting Chicago (unless it’s to take a day trip).
How many days do you need to spend in Chicago?
Give yourself at least 4-5 days to spend in Chicago. This will give you plenty of time to explore some of the neighborhoods, enjoy the food scene, catch a game, see a show, and take a day trip.
Does Chicago have a beach?
Yes! Chicago’s 26 miles of scenic lakefront includes several public parks and gardens, an 18-mile Lakefront Trail, and more than two dozen free beaches. All Chicago beaches are open for the summer season from late May to early September.
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This article about cool hotels in Chicago is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this post about cool hotels in Chicago are affiliate links, and, at no cost to you, I may earn a small commission.
