The Best Chicago Hotels

Christine Drinan, Founder

Peninsula chicago

Chicago is one of the best hotel cities in the United States, where you get actual value for your dollars spent.  The hotels are good enough to devote an entire article, and actually a reason to visit the city of Chicago.  Overall, rooms are generously sized and beautifully appointed.  The service is genuine Midwestern welcome.  We don’t do four star hotels at Galavante unless that’s all there is available, but the four star options in Chicago are even good.  These are the best Chicago hotels, and hotels period in any major U.S. city.

Peninsula Chicago

The Peninsula

This is like Vanity Fair’s best dressed icon list.  Located right off Michigan Avenue, this is the best Chicago hotel in the city in all categories. It gets top scores for overall luxury, hotel amenities, dining, rooms, spa and appointments.  This is where we stay 90% of the time we are in Chicago because the rooms are the best.  We have mad respect for the cleaning staff as this is one of the most spotless places you can stay in the world.  In our test, we would actually walk around barefoot in the hotel rooms.  That is, if their slippers and robes weren’t so darned comfortable.

Service is text book polished – you won’t find flaws.  The one note we have,  is that there is a passion and heart that is missing.  The team does their job, but in 50+ visits, we can’t point to anyone who even remembers us.  But if you’re not looking to be best friends with the entire team when you leave, this is the place to stay in Chicago for luxury. The hotel reopens in August sometime from this COVID mess.  We bet that with the incredible housekeeping staff, they will be top of the game.

Park Hyatt Chicago

The Park Hyatt

The Park Hyatt became a favorite from the day the hotel opened over 20 years ago.  The restaurant Nomi is consistently one of the best power breakfast options in the city, and a spot for a late night low-key nightcap.  They have a beautiful terrace when the weather is warm.  The Park Hyatt locked their formula down on chic modern interior, excellent lounge bites, master sushi chefs and polished service from day one.   That’s before the stunning views of Lake Michigan and the Water Tower and prime location.

Rooms in recent stays are a tad bit tired though still lovely.  Nowadays it’s our choice because it’s the most reasonably priced of the luxury hotels.  For Michigan Avenue options, this is the hotel with the most modern décor for those who want that aesthetic.  We stay here at least twice a year on trips to the Windy City.  Also for those who are into earning points, Park Hyatt is always a good option.

Nobu Chicago

Nobu Chicago

This is the hottest hotel in town right now.   The rooftop and restaurant are some of the most coveted reservations in the city  We are huge devotees to their rock shrimp tempura and yellowtail jalapeño.  We were skeptical though to think they could pull off a hotel we would like as much or more than the Peninsula.  To shortcut it, we love this hotel.

Nobu just opened around July 1st so we were also expecting a whole host of opening issues.  We were blown away, and no, it wasn’t because expectations were low.  From the moment you roll up next to the Bentleys parked outside, the team is on their game.  They were all so passionate and grateful for the hotel to open, and excited to welcome guests.  They are uniformly nice to everyone, even if not all those guests are exuding the warm and fuzzies in return. Whoever the GM is, he/she is doing something right.  Their team was genuinely united to make this crazy time in COVID work.  We can only imagine what it will be like when things come back to normal, as they’re crushing it right now on service.

Rooms are on the smaller size, which is surprising for a new build.  However the neighborhood location lends itself to having you explore the area.  Prices for a five star level hotel are reasonable and an excellent value for a luxury option.  They are hands down the nicest place to stay in the West Loop, which is one of the best places to base for the culinary options in nearby Fulton Market.

Our one piece of feedback is that they need to figure out the sound proofing (one of those opening jitters).  You can hear neighbors and this may not be the place to stay if you’re super sensitive to noise. The West Loop is a booming construction zone of luxury condominiums.  But if you’re in it to have a good time in the trendiest neighborhood in Chicago, this is your spot.

Four Seasons Chicago

The Four Seasons

This is as quintessential Four Seasons as it gets.  We love staying here when we’re going to host family for their famous Sunday brunch.  The brunch is neck and neck with The Peninsula as the best in the city, and maybe just a nose ahead.  Their afternoon tea service is comfortingly old school fancy.  We also like that the lobby lounge and bar areas make for a discreet and cozy nightcap.  Rooms are lovely, like they always are at the Four Seasons.  If you’re looking for a blowout experience, you’ll want to get a suite.  We would say that this is also one of our top choices for Families, as the Four Seasons just knows how to welcome your kids in style.


The Ritz Carlton which was a construction zone last time we were there and such an unpleasant experience that we checked out early.  We’ll revisit this when they re-open to their full glory as we always loved that afternoon tea.

We’ve stayed at pretty much every hotel worth staying at in Chicago, so for our insight into other hotel options, hit us up at [email protected] and we’ll get you the inside track.

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An Affordable (Relatively Speaking) Hotel In the Hamptons
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The Peninsula Hotel – Because We’ll Always Be Friends


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