Coolest Hotels in Chicago

Ah, The Windy City! Chicago is a city made up of many different types of neighborhoods and many different types of accommodations so it can be overwhelming deciding where to stay. I’ve done the work, and below are (IMO) the coolest hotels in Chicago. Some I’ve stayed at, some I’ve only had dinner or drinks, but ALL I would recommend to my friends, depending on what they are looking for.

If short term-rentals are more your thing, check out the coolest VRBO’s in Chicago.

Note: Please confirm with the hotel prior to booking as certain features and amenities may be closed due to global health & safety issues.

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Hotels in the West Loop

The West Loop (the neighborhood just west of The Loop) has become the spot for the best restaurants, bars, and nightlife in Chicago. There won’t be a ton of shopping here (go to The Mag Mile for that), and it’s not close to the lake, but if you are looking for the sceniest scene, this is it. It only recently became IT, so there’s still a little grunge (in a good way) on the edges. There are quite a few cool hotels in Chicago located in the West Loop, below are my top three.

Ace Hotel Chicago

I’m a sucker for a good rooftop, and Ace Hotel has a great rooftop restaurant. As a boutique hotel chain, Ace Hotel has an industrial/cool/trendy vibe. Across from Google headquarters, it won’t have the best view from every room, but usually, it’s a great price for a neighborhood that a lot of people want to stay in.

The Hoxton Chicago

Another boutique hotel, The Hoxton Chicago is only one block away from Fulton St. and near a ton of great restaurants. One of the coolest things it has going for it is its outdoor rooftop pool, and if you visit Chicago in the city know there is nothing more luxurious than a pool as an oasis in the city. When you stay at The Hoxton you really feel like you are staying in a hotel in the coolest part of the city.

Nobu Hotel Chicago

It’s no surprise that Nobu Hotel Chicago is right on Randolph Street, aka Restaurant Row. As the West Loop’s 5-star hotel, Nobu has a killer rooftop bar, the highly acclaimed Nobu restaurant, and you’ll feel right at home with the finest in-room amenities from the Dyson hairdryer to the Nespresso machine.

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Hotels on the Chicago River

The Chicago River is a unique waterway that connects the Great Lakes to the Mississippi River Basin. Although most of it runs north/south, the main stem runs east/west through the city center. Not only is it cool to see, but Chicago has semi-recently built up the Riverwalk, which is a 1.25-mile pathway right on the river that is sprinkled with restaurants and bars. It’s also a central location, with the Mag Mile to the North and the Loop/Theater District to the south. If you don’t end up staying on the Chicago River, you’ll still definitely want to check it out via an Architectural Boat Tour, trust me.

LondonHouse Chicago

On the south side of the river, LondonHouse is the spot to get amazing river and iconic bridge views. You may or may not get the views from your room, but you most definitely will get the views from their rooftop restaurant and bar.

The Westin Chicago River North

One of the best things about staying in a chain you’re familiar with is you know what you are going to get and this hotel fits the bill. You walk in and it smells just like a Westin, which as a frequent traveler can be comforting! And like most other Westin’s this one is a massive hotel with good service and well-appointed rooms. And since it’s on the river, the possibility of an amazing view too.

The Langham Chicago

The Chicago River’s 5-star hotel is The Langham Chicago. No gimmicks here, just pure luxury with outstanding service, floor-to-ceiling windows in each room, and a 5-star spa.

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Related: How to Plan a Vacation (including free timeline planner)

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Hotels on the Magnificent Mile & Michigan Ave.

Michigan Avenue is a 12-mile street running north and south through Chicago, and the Magnificent Mile is the northernmost section connecting the Michigan Ave bridge to Oak Street. When you stay on the Magnificent Mile you will be in the heart of shopping, dining, and yes, tourism. If you are a first-time visitor, this will be the most central location to stay. Think, New York Times Square, but add in some charm and remove the stuffed fake Elmo’s.

Four Seasons Hotel Chicago

Located at the northern part of The Mag Mile, the Four Seasons Hotel Chicago is in the 900 North Michigan Ave. building and a stone’s throw to the shops on Oak St. and Oak St. beach, which means one thing, bougie. As a 5-star hotel, the Four Seasons is also one of the top luxury hotels in Chicago with the unrivaled city and lake views and a world-class spa.

Intercontinental Chicago Magnificent Mile

Across the street from The Shops at North Bridge and two blocks to the Chicago River, the Intercontinental is near the end of The Mag Mile (but nowhere near the end of Michigan Ave.) What’s nice is that since it’s just north of the Chicago River it’s only a 15-minute walk to Cloudgate (otherwise known as The Bean). The rooms are fine (aka clean) but finding a hotel in this location, with great city views and is pet-friendly…well that is hard to come by.

Omni Chicago Hotel

Fun fact: when I was younger and Oprah filmed her show in Chicago, during every show they announced that guests of the Oprah Winfrey show stay at the Omni hotel. And that’s what I think of when I think of the Omni. If it’s good enough for Oprah, it’s good enough for me! Located in the middle of The Mag Mile, you will be close to shopping, Oak Street Beach, and the Chicago River.

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Historic Chicago Hotels

Chicago is a city full of history (relatively speaking, since the U.S. is a newer country). As one of the largest cities in the U.S., Chicago is by far the largest city in the Midwest and has been an integral part of the nation since 1850. Although much of it was burned to the ground during the Great Chicago Fire of 1871, Chicago rebuilt and has worked to retain much of its rich history. Staying in a place that was built in the 19th or early 20th century has the charm that just can’t be replicated.

Palmer House

Located in the Loop, staying at Palmer House you’ll be right across from the Art Institue and the el will be nearby (note you may hear the train). Palmer House was actually being built during the Great Chicago Fire and had to be rebuilt after it was burned. And rebuild they did. Walking in you can feel the history of hundreds of years gone by.

StayPineapple The Loop

A boutique hotel in The Loop? Who would’ve thought? StayPineapple is a fun hotel in Chicago, but that doesn’t take away that it is in a National Historic Landmark Building. It’s 4 blocks away from Cloudgate and Millenium Park, so it will be easy to have fun inside and outside of the hotel. Oh, and it’s pet friendly, because can a hotel really be fun if your best friend isn’t allowed. Side note: am I the only one who thinks of RHONJ anytime I hear of pineapple lately?

The Drake Hotel

While The Drake may not officially be a 5-star hotel, it feels ever so elegant. Located on the north end of The Mag Mile, The Drake is the quintessential Chicago Hotel. Opening its doors in 1920, 100 years later it still serves high tea in the Palm Court by day and cocktails and dancing at night. If you want to feel the grandeur of Chicago, what it once was and still is, this is it.

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Luxury Hotels in Chicago

If you can afford it, why not? Getting pampered in a 5-star hotel makes your vacation complete. Whether you are hitting the town running or taking it a little more low-key, when you get back to your room don’t you just want to feel at home? Or, actually, better than home? It’s a vacation after all.

The Peninsula Chicago

There’s a reason Travel & Leisure ranked The Peninsula as the #1 hotel in Chicago in 2020. With world-class dining and spa options, this is the place to stay. It’s pet-friendly (because even pets deserve to be pampered). Not only is it in a great location along the Mag Mile, but they even offer exclusive outings via The Peninsula Academy.

Waldorf Astoria Chicago

The Waldorf Astoria is located in the Gold Coast, near Rush & Division, by all of the designer shops. It’s only a few blocks from Oak St., Oak St. beach. and Lake Michigan. Built in the style of a French chateau, the Waldorf Astoria is also home to Margeaux Brasserie, where you can get one of the best steak frites in the city.

Park Hyatt Chicago

Situated on Michigan Ave. (technically there is a small park between Michigan Ave. and the hotel), the Park Hyatt is on the Magnificent Mile in front of the historic Chicago Water Tower (one of the few buildings that survived the Great Fire). As you would expect with all 5-star hotels, the service, food, and accommodations are top-notch. An anecdote: as a little girl, I would walk under the Park Hyatt’s heated overhang where guests waited in their fur coats for a taxi, and to me, it just screamed luxury to heat the outdoors. As an adult, I still die for an outdoor heater.

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Where the Cool Kids Stay

OK, so this whole post is dedicated to cool Chicago hotels, but in every list, there has to be a ranking. When all you care about is the hotel being v cool, these are for you.

Hotel EMC2

As the name implies, this hotel is all about art and science. From the robot attendants to the restaurant named in honor of Albert Einstein, EMC2 is at the cutting edge of technology (you’ll even have an Amazon Alexa in your room). Located two blocks of The Mag Mile and near Northwestern Hospital (ah, the sounds of the city), it is centralized, but most people stay because it’s just cool.

Viceroy Chicago

A 5-star hotel with an outdoor rooftop pool in Chicago’s Gold Coast? OK so maybe people stay at Viceroy Chicago for reasons other than it’s cool. It’s also luxury with a capital L. So like, cool luxury. Designed in black and gold with floor-to-ceiling windows, the rooms are v cool. Check out the rest of the hotel with the rooftop lounge and if time permits, have them arrange a visit to Aire Ancient Baths to experience a greek and roman style bathhouse, right in Chicago.

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Where To Earn or Redeem Hotel Points

In an ideal world, we would stay where we want to stay, regardless of any other factors. The harsh truth is sometimes we want to use points on a trip or sometimes we’re thiiiiiis close to status so we need to book some stays with a chain. When that is the case where are the coolest Chicago hotels to stay that don’t remind you of why you are staying there? Earn your Marriott and Hyatt points at these cool hotels.

Hotel Zachary

You cannot get any closer to Wrigley Field than Marriott’s Hotel Zachary. And because of this phenomenal location, one might think the hotel doesn’t need to be that great. But it is. Paying homage to its location, the hotel is designed in traditional colors and materials but has all the modern conveniences you’d want. And even if you aren’t going to a game, you’ll still get the energy as you look out at the field from your room or the bar. Truly a unique experience.

Chicago Athletic Association

The website doesn’t look like it’s part of Hyatt, but it is. With restaurants like Shake Shack on street level and Cindy’s Rooftop on the top, even locals find the Chicago Athletic Association is a destination. Situated on Michigan Ave right across the street from Millenium Park in a historic building, I like to this of this as a boutique hotel wrapped in the benefits of a chain.

The Gwen

The Gwen is in another historic building (see, Chicago’s rich with history) but is part of Marriott’s The Luxury Collection. Not only is it modern with better than your typical Marriott amenities, but the rooftop restaurant and bar also has gorgeous views of the city. They’ve also introduced the modern tea party, Tipsy Tea at the Gwen offers tea concoctions like ‘High Maintaince’ which is chai spiked with rum. Now, how cool is that?

Thompson Chicago

Part of the Hyatt family, Thomspon Chicago is located in the Gold Coast amongst beautiful homes but very close to the Mag Mile, Oak Street Beach, and Lake Michigan. It might just be the most aesthetically pleasing hotel on the list, furnished in rich velvets and leathers and designed by world-renowned Tara Bernard.

Hotel Lincoln

Hyatt’s Hotel Lincoln, in the Land of Lincoln, across from Lincoln Park…sense a theme? All joking aside, Lincoln Park is Chicago’s largest park and home to the free Lincoln Park Zoo. The hotel is nicely appointed and has an awesome rooftop bar too. Need I say more?

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Coming to Chicago? Check out these posts to help with planning.

• The Best of Chicago (what to do, where to go, what to eat)
• 3 Day Chicago Itinerary for the Spring & Summer
• Fall & Winter 3 Day Chicago Itinerary

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Before you travel, make sure your toiletry bag is stacked!

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