The 10 Best Places to Stay in Chicago (For Every Budget)

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The first time I visited Chicago I went in February, which everyone who lives there warned me against and which I did anyway, and the wind coming off Lake Michigan was so aggressive that I bought a hat from a drugstore on my first afternoon and wore it, indoors, in the hotel lobby, while my sister Jenna laughed at me from a chair by the fireplace. We still had the best week. That’s the thing about this city, it wins you over even when it’s actively trying to freeze you.

I’ve been back plenty of times since, in kinder weather mostly, and I’ve slowly built up a list of the best places to stay in Chicago that I keep tweaking after every trip and every report back from friends.

The 10 Best Hotels and Stays in Chicago, For Every Budget

1. HI Chicago Hostel (My First-Timer Answer)

I usually tell people that where to stay in Chicago for the first time comes down to one word, the Loop, because it’s the downtown core where the trains all meet and half the famous sights are within a walk, and if you want to sleep right in the middle of that without paying downtown hotel prices, HI Chicago is the answer I keep giving. Most budget hotels in Chicago push you out toward the edges of the city, but this one doesn’t, and if you’re searching where to stay in Chicago on a budget without giving up the walk-everywhere location, this is it.

It’s a big, well-run hostel on Ida B. Wells Drive, a few minutes on foot from Millennium Park and the Art Institute, with a 4.4 rating from over 3,000 guests, dorm beds with their own reading light and outlet, free coffee in the morning, and staff who run little events and neighborhood tours so solo travelers aren’t left rattling around a strange city alone on the first night.

You can see the L train from the breakfast area, which runs all night, so light sleepers should pack earplugs and pick a curtained bunk, but for the price and the location I’ve never found a better landing spot for a first Chicago trip, and my brother Ryan, who is picky about hostels in a way that borders on a personality trait, gave it a nod, which almost never happens.

2. Freehand Chicago (The Social Budget Pick)

The Freehand sits in River North, which is the restaurant-and-nightlife district just north of the river, and it’s a hybrid of hostel and hotel, so you can book a shared dorm-style room with a locker or a private room, and either way you get access to the Broken Shaker bar downstairs, which is genuinely one of the better drinks spots in the city and not just a hotel afterthought. That mix makes it a favorite for the kind of traveler who wants somewhere social on a budget but has aged slightly out of the top-bunk-in-a-ten-bed-room stage of life.

A note of honesty, because the reviews are a mixed bag: the vibe and the location and the bar are the reasons to book, and a few guests have flagged housekeeping misses, so it’s worth being a little particular at check-in.

3. Hotel Lincoln (Rooftop Views Over Lincoln Park)

Hotel Lincoln sits across the street from Lincoln Park itself, which means the park, the free zoo, and the lakefront are all right there, and the rooftop bar, called the J. Parker, has one of the best skyline-and-lake views in the city, the kind of view people line up for. It’s a quirky, vintage-flavored place with a lobby full of odd collected objects, and the rooms lean cozy over spacious, which is the Chicago neighborhood-hotel trade-off in a nutshell.

One practical warning that comes up in the reviews often enough to repeat: ask specifically for a renovated room when you book, because the older standard rooms are a noticeable step down from the updated ones. Get that right and you’ve got a lovely, well-priced base a short bus ride from downtown with a park across the road.

4. Hotel Zachary (Right at Wrigley Field)

If anyone in your group cares even slightly about baseball, Hotel Zachary is the one, because it sits directly across from Wrigley Field in Wrigleyville and some of the rooms look straight at the ballpark, and its 4.6 from nearly 900 guests lands it among the best hotels in Chicago in the eyes of the people who rave about the location and the little touches, chocolate-covered strawberries left for a birthday, a surprise room upgrade, that sort of thing. Even outside baseball season the block is packed with good restaurants, and the neighborhood has a lived-in, cheerful energy that the downtown hotels can’t quite replicate.

Mark and I aren’t really baseball people, but we ended up at a game on a whim on a trip years ago, and I still remember the walk back to our room afterward taking roughly ninety seconds, which after a long day on your feet is its own small miracle.

5. The Publishing House (The B&B in the West Loop)

This is my sentimental favorite on the entire list, a small bed and breakfast in the West Loop with a 4.9 rating from nearly 400 guests, set in a converted old building with individually designed rooms, heated bathroom floors, a genuinely excellent cooked breakfast, and complimentary drinks in the common room in the evening. The West Loop around it has quietly become the best food neighborhood in the city, all converted warehouses and destination restaurants, so you can walk out the door and eat extraordinarily well without a plan.

People coming from big anonymous chain hotels always seem a little stunned in the reviews at how personal and warm it feels, and how much design they got for the price, and I understand that reaction completely, because I felt it too. It books up well ahead, so if the dates matter, reserve early.

6. The Robey (The Bucktown Design Landmark)

Out of all the boutique hotels in Chicago, the Robey is the one I get most excited to describe, because it lives inside a slim 1929 Art Deco tower at the six-corner intersection of Bucktown and Wicker Park, the hip, muraled, vintage-shop part of the city, and its rooftop bar looks out over a skyline view most tourists never even find. The rooms are crisp and design-forward, some with wonderful curved windows following the shape of the old building, and one reviewer put it perfectly by basically begging people to stop defaulting to the Loop and come stay out here instead.

The practical bonus is the Blue Line station steps from the door, which runs straight to O’Hare in one direction and downtown in the other, and is far more reliable than sitting in a cab on the expressway hoping to make your flight.

7. Kimpton Gray (Where the Splurge Begins)

From here on we’re in splurge territory, though the Kimpton Gray eases you into it gently, because it’s a handsome hotel built into a 1894 marble-clad building right in the financial district heart of the Loop, walkable to essentially everything downtown, with a 4.5 from over 2,000 guests and the kind of service that reviewers single out again and again by name. There’s a free evening hosted hour, a rooftop lounge, and rooms that manage to feel calm in the middle of all that downtown stone and noise.

It’s the sort of place I’d book for a first proper grown-up trip to Chicago, central enough that you barely need transit, nice enough to feel like a treat, without tipping into the eye-watering prices of the true grande dames further up this list.

8. The Langham (The One for a Special Occasion)

The Langham occupies the lower floors of a famous Mies van der Rohe tower right on the Chicago River, and it holds a 4.7 from more than 2,600 guests, which for a hotel this large is remarkable, and the reviews read like a steady drumbeat of people describing the best service of their travelling lives, the riverfront views, the spa, the sense of being quietly and completely looked after. This is the address I hand to anyone marking an anniversary or a big birthday.

Jenna and I split a high tea here on a trip years ago that we had absolutely no business affording, and the staff never once made us feel like the tourists we obviously were, and the little tower of sandwiches kept refilling until we genuinely had to ask them to stop.

9. The Drake (The Grand Old Landmark)

The Drake opened in 1920 at the top of the Magnificent Mile where it meets Lake Michigan, and it is pure old-Chicago grandeur, the kind of lobby where you half expect to see signatures from the likes of Muhammad Ali and Princess Diana, both of whom actually stayed here, along with more or less every visiting dignitary of the last century. It holds a 4.3 across an enormous pile of reviews, and I’ll be straight with you, some of them note that the grande dame is showing her age in places, which is true of a lot of century-old hotels.

But the location at the top of the shopping mile, steps from the lake and Oak Street Beach, is genuinely hard to beat, and there’s a sense of history in that building that a brand-new tower simply can’t manufacture. You’re paying partly for the ghost stories, and I think they’re worth it.

10. Waldorf Astoria Chicago (The Gold Coast Finale)

To close the list I’ll point you to the fanciest address of the lot, because if you’re comparing the true luxury hotels in Chicago, the Waldorf Astoria in the Gold Coast is the one that comes up first, a hushed, French-inspired building on a quiet street just off the Magnificent Mile, with a 4.7 rating, in-room fireplaces, a spa people write love letters about, and the sort of concierge team that quietly arranges the kind of upgrades and small surprises that turn a nice trip into a story you tell for years.