The 17 best Chicago hotels

Chicago is home to a hefty variety of hotels for travelers craving a stay in the Windy City.

Thanks to a slew of openings and renovations over the last few years, Chicago’s hotel scene is hotter — and more luxurious — than ever before. But this is no one-trick pony when it comes to the hotel experience.

Travelers, once they settle the debate over whether to fly into O’Hare or Midway, can find a variety of value hotels in the heart of downtown, or they can splurge for something extra special with a Lake Michigan view. Just as one can take a day off and frequent the Art Institute of Chicago like Ferris Bueller, there are plenty of other paths a trip can take: Deep-dish pizza or Lollapalooza, anyone?

Whether you’re in town for business, to catch a Chicago Cubs game, or here to admire T-Rex SUE and the Egyptian mummies at the Field Museum, there’s a great hotel for every type of traveler.

Here are the 17 best Chicago hotels and how to book them.

Park Hyatt Chicago

Gold Coast, Chicago, Illinois, USA

Best for: Luxury and business travelers looking for easy access to the Magnificent Mile.

Why stay here: After a recent renovation, the Park Hyatt Chicago features brightened-up guest rooms and suites that feel more like a cozy getaway than a business-minded city hotel.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits while earning and redeeming World of Hyatt points. If you have access to bookings through American Express Fine Hotels + Resorts or Chase’s Luxury Hotels & Resorts Collection, you can score extras like complimentary daily breakfast for two and space-available upgrades.

There might be many Park Hyatt flags flying around the world, but Chicago is the original home of this luxury brand. The Park Hyatt Chicago underwent a $60 million renovation in early 2022 that resulted in refreshed guest rooms and suites, and menus at the hotel’s NoMI restaurant and lounge. It’s likely indicative of where the broader Park Hyatt brand is heading.

The lobby got a slight facelift of its own that resulted in brighter columns and a generally more inviting place to make a first impression. The 146 guest rooms and 36 suites feature walk-in showers with waterfall showerheads. Soaking tubs are a luxurious way to unwind after a busy day at the office or exploring the city, and the rooms now feature a mix of green, gray and cream colors to reflect Chicago’s mix of parks and soaring towers of steel and sandstone.

For those looking for more of a wellness getaway with their stay, the Park Hyatt also offers facial and body treatments in NoMI Spa (not to be confused with the restaurant or rooftop lounge).

Rates at the Park Hyatt Chicago currently start at $486, or 21,000 World of Hyatt points, per night.

The Peninsula Chicago

Gold Coast, Chicago, Illinois, USA

Best for: Spa lovers looking for resort vibes in the heart of downtown Chicago.

Why stay here: The convenient location on the corner of Michigan Avenue and E. Superior St. is hard to beat, but the Peninsula is a destination on its own with amenities galore to keep you from ever having to leave (well, at least until check-out). The Peninsula Spa beckons those seeking a wellness getaway while Z Bar’s terrace is a draw for those whose idea of wellness begins with a chic cocktail at happy hour.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits. If you have access to bookings through American Express Fine Hotels + Resorts or Chase’s Luxury Hotels & Resorts Collection, you can score extras like complimentary daily breakfast for two and space-available upgrades.

Sure, a lot of places try to stake the claim of being an oasis in the heart of a city, but The Peninsula Chicago might actually be just that.

The Peninsula Spa is a draw for both visitors and locals, as the facility includes an outdoor sun terrace for warmer weather, a half Olympic-length pool, gym and yoga room, and a relaxation lounge complete with a fireplace perfect for the most frigid Windy City winters. That’s only one piece of the Peninsula’s ultra-luxurious hospitality streak.

Like several other deluxe hotels in the vicinity, The Peninsula’s main public spaces are a few floors above the hecticness of Michigan Avenue. While there’s usually plenty to buzz about at the hotel — The Peninsula’s Z Bar is a highly coveted spot for cocktails with a view, while The Lobby is the pinnacle of Chicago’s power breakfast set — it feels a little more refined away from the street level stress.

The guest rooms are spacious and elegant with neutral colors, tastefully placed floral arrangements and thoughtfully arranged seating areas. The bathrooms are equally as luxurious, with separate soaking tubs and walk-in showers.

Of course, you can truly glam up a visit with a stay in something more opulent like The Peninsula Suite, a 3,645-square-foot home away from home on the 18th floor with a private terrace, baby grand piano and a living room and dining room perfect for entertaining guests. Even the soaking tub in the Peninsula Suite comes with a view.

Rates at the Peninsula Chicago currently start at $575 per night.

Pendry Chicago

The Loop, Chicago, Illinois, USA

Best for: Art Deco luxury on the edge of the Loop.

Why stay here: In the era of blurred travel purposes, the Pendry Chicago is a great place to stay when heading to Chicago for business, leisure or a combination of both. The convenience to the Loop, Michigan Avenue, the Chicago River (and all those architecture tour boats) and Millennium Park provides a little bit of something for everyone.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits or through the Pendry website, or through the Chase Luxury Hotel and Resort Collection.

When the building resembles a champagne bottle, one can hope the service inside is just as chic and bubbly as the exterior implies.

The Pendry Chicago delivers from its home within the historic art deco Carbide & Carbon building, but it’s easy to miss the front door because the tower itself is so striking (black granite, green terracotta and gold leaf). The building’s architects, brothers Hubert and Daniel Burnham Jr., reportedly wanted the structure to resemble a bottle of bubbly with gold foil on top.

After checking in at the living room-like lobby, turn the corner to the gilded hallway with a bank of golden elevators ready to whisk you up to your room. Other spaces within the hotel are far more subdued, so the Roaring ’20s vibe largely disappears once you leave ground level.

Guest rooms are designed with a clean, minimalist aesthetic: white, black, gray, and bronze, with the occasional pop of burnt red driving much of the color scheme. Marble bathrooms feature walk-in showers and MiN New York amenities.

While there are several ways to drink and sip at the Pendry, Château Carbide is one of the more Instagrammable. Aiming to combine the French Riviera with Chicago, the rooftop bar operates year-round (swap out Aperol spritzes for hot toddies in the winter). Bar Pendry, on the other hand, is a more dimly lit hideaway with wood-paneled walls, cozy seating areas and a fireplace fit for sipping cocktails over secrets adjacent to the lobby.

Rates at the Pendry Chicago currently start at $242 per night.

Waldorf Astoria Chicago

Gold Coast, Chicago, Illinois, USA

Best for: A classic, luxury stay that’s a little removed from the hustle and bustle but still close to Oak Street shopping.

Why stay here: There’s a luxe residential ambiance to the Waldorf that makes this feel more like staying at a friend’s fabulous downtown condo rather than at a high-end hotel.

Best way to book: Book through our partner Skylark to earn Hilton points while enjoying elite-like benefits and on-property credits. American Express Platinum cardholders booking through American Express Fine Hotels + Resorts can receive value-added benefits like upgrades and late checkout based on availability plus on-property statement credits.

The hotel industry might be moving in the broader direction of bringing down the walls and better-connecting guests to a surrounding neighborhood. The Waldorf Astoria Chicago doesn’t appear to have gotten the memo … and that’s perfectly OK.

It’s a few blocks from downtown Chicago, which gives guests more of the vibe of living like locals — very posh locals, that is — instead of staying blocks away from some of the most tourist-trekked parts of the city.

Most rooms come with a fireplace and exude classic luxury with a largely black-and-white design scheme. Velvet couches, chandeliers and black-lacquered doors add to the chicness throughout the hotel.

If you’re looking for a well-connected friend to nab tickets to a show or game — or a hard-to-come-by reservation — the Waldorf concierge is just the person to do your bidding. Waldorf habitués might notice an outpost of Peacock Alley — the lounge from the original Waldorf Astoria in New York City and increasingly an offering at Waldorf hotels elsewhere in the world — wasn’t originally in the Chicago branch of the luxe brand.

That changed ever-so-slightly in October 2022 with the arrival of the Peacock Lounge, which opened as part of a broader renovation to the hotel’s guest rooms and spa. Peacock Lounge pays tribute to Peacock Alley while two other new dining options — the Scottish-themed Bernard’s Bar (which initially closed down 13 years ago and now gets a revival) and the American-focused Brass Tack restaurant — also opened amid the renovation.

Rates at the Waldorf Astoria Chicago currently start at $566 per night.

Four Seasons Hotel Chicago

Gold Coast, Chicago, Illinois, USA

Best for: A luxe stay with Lake Michigan views and easy access to Michigan Avenue couture.

Why stay here: For a luxury hotel that sits on top of a high-end mall, the Four Seasons Chicago still feels like a getaway from all the noise and activity of Michigan Avenue below.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits or directly through Four Seasons. American Express Platinum cardholders booking through American Express Fine Hotels + Resorts can receive value-added benefits like upgrades and late checkout based on availability plus on-property statement credits.

Luxuriate in proximity to some of Chicago’s best districts with a stay at the Four Seasons Hotel Chicago. Oak Street Beach is just a short walk away, while the more cardio-driven guest can go on a run along the Lake Michigan shoreline. For those whose idea of exercise is shopping ’til they drop, Oak Street is just around the corner and features high-end boutiques and restaurants.

The palatial Four Seasons guest rooms come with nonpareil views of the Chicago skyline or Lake Michigan, and it’s easy to feel like a demigod in the hotel’s Roman-inspired pool (there’s just something extra luxe about doing the backstroke under a domed ceiling, no?).

Plus, if you forgot to pack something for a night out on the town, it’s nice to have Bloomingdales, Gucci and the rest of the 900 North Michigan Shops mall right downstairs.

Rates at the Four Seasons Chicago currently start at $530 per night.

Nobu Hotel Chicago

Fulton Market District, Chicago, Illinois, USA

Best for: Luxurious, minimalist design in the heart of Chicago’s Restaurant Row.

Why stay here: A famous restaurant may be in the name of the hotel, but the Nobu Hotel Chicago is a draw for a variety of non-foodie tastes as well.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits or directly with Nobu Hotels.

Don’t let the restaurant behind the name of the hotel fool you: Nobu’s 115 guest rooms and suites excel in design and luxury just as well as their dining hot spot of a sibling.

Nobu Hotel Chicago’s calm aesthetic begins in the lobby where sleek, dark walls and furnishings are punctuated by the occasional pop of floral or gold leaf. Guest rooms exude Japanese minimalism with plush, white bedding and sleek black headboards. Walk-in showers and Natura Bissé bath amenities await in the bathroom. Splurge for a suite, and treat yourself to a soaking tub with views of the Chicago skyline.

Along with being home to the Nobu Chicago restaurant, the hotel features a rooftop serving up cocktails and small plates. If you’re still hungry after that, the hotel’s West Loop location is convenient to other top-tier dining rooms along Chicago’s Restaurant Row, like Stephanie Izzard’s Girl & the Goat.

Rates at the Nobu Hotel Chicago currently start at $331 per night.

The Langham, Chicago

River North, Chicago, Illinois, USA

Best for: Luxury travel for those with an eye for mid-century design (and fabulous views).

Why stay here: Architecture buffs will love everything in and around the Langham Chicago, as the renowned skyscraper in which it sits is just a few steps from where travelers flock to board one of the city’s numerous architectural boat tours.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits or directly with Langham. Booking through American Express Fine Hotels + Resorts or Chase’s Luxury Hotel and Resort Collection confers value-added benefits like upgrades and late checkout based on availability plus on-property statement credits.

Within the Ludwig Mies van der Rohe-designed 330 North Wabash skyscraper (better known as the IBM Building), the Langham appears to follow Mies’s motto of “less is more.”

Guest rooms and suites are bright and tastefully refined and offer incredible up-close views of the Chicago skyline. A largely earth-tone color palette runs through most room and suite offerings, with the occasional accent of dark wood furniture or a purple blanket artfully arranged here or there.

Soaking tubs and rainfall showers characterize the palatial bathrooms. Higher-end suites like the Regent Suite and Infinity Suite include elegant gold-leaf ceilings in living areas and ornate floral wall decor.

Architecture buffs should book a table at Travelle, the Langham’s farm-to-table restaurant that includes views of the neighboring circular towers of Marina City (made famous in pop culture for their feature as the album art on Chicago-based Wilco’s “Yankee Hotel Foxtrot”). But also save time to unwind at Chuan Spa, part of the Langham’s wellness facility that also features an indoor pool and gym.

Rates at the Langham Chicago currently start at $473 per night.

Viceroy Chicago

Gold Coast, Chicago, Illinois, USA

Best for: Tony accommodations and rooftop fun in Chicago’s Gold Coast district.

Why stay here: The Viceroy makes a good first impression immediately after crossing over the welcome mat. Rooms are cozy, and the Gold Coast location is a nice step back away from the tourist scene of Michigan Avenue.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits or directly via Viceroy Chicago’s website.

While Michigan Avenue might be the most upfront with its luxury offerings, thanks to all the fashion boutiques, there are plenty of high-end hotel offerings just off Chicago’s main thoroughfare. Viceroy Chicago, in the city’s glitzy Gold Coast neighborhood, manages to wow without going overboard with ostentation.

A strong color palette of deep blue and gold, along with rich velvet fabrics on couches and chairs, makes this an inviting, luxurious place to stay. Guest room decor is a mix of Southwestern chic, retro glam and city grit with picture windows and gold accent walls — a funky mix that still pulls together nicely.

The Gold Coast is known for being a major draw for foodies and bar-hoppers alike, and Viceroy Chicago delivers on both: The Devereaux lounge on the 18th floor serves up cocktails and small bites (who doesn’t like a black truffle deviled egg alongside their frozen rosé?) in the presence of a rooftop pool while Somerset restaurant downstairs serves updated American fare like burgers, steak and seafood.

Rates at Viceroy Chicago currently start at $239 per night.

The Hoxton, Chicago

Fulton Market District, Chicago, Illinois, USA

Best for: A hip, snug stay for creative types looking to explore the Fulton Market district and Restaurant Row.

Why stay here: Mid-century meets industrial at this cozy hotel (that’s usually priced at a value compared to other high-end hotels in the city).

Best way to book: Book directly with The Hoxton, and keep an eye for integration with Accor (which now has a roughly two-thirds stake in the company) and its Accor Live Limitless loyalty program.

The 182 rooms at the Hoxton, Chicago, are cozy — if not downright small — but well decorated and efficiently laid out. Leather paneling, custom-designed bedding by local artist Cody Hudson and large windows compensate for limited square footage.

Plus, the Hoxton beckons guests out of the room and into hip public spaces like its rooftop Peruvian restaurant Cabra Cevicheria (another Chef Stephanie Izzard mainstay). Music lovers will find plenty to enjoy at Lazy Bird, an opulently decorated cocktail venue with a stunning teal, underlit bar at its center. Of course, the weekend live music acts that perform here are likely getting everyone’s attention more than the design of the bar.

Think of the Hoxton as though CitizenM or Moxy had a high-end sibling — or if WeWork ended up being a success and got into the business of hotels. In fact, the Hoxton, Chicago, even offers a co-working feature for those looking for a place to work ($30 for the day, and that comes with unlimited tea and coffee).

Rates at The Hoxton, Chicago, currently start at $188 per night.

Sofitel Chicago Magnificent Mile

Gold Coast, Chicago, Illinois, USA

Best for: Those looking for a high-end stay and convenient access to downtown without being right on Michigan Avenue.

Why stay here: The Sofitel might draw guests in with its slanted lean over Chestnut Street, but there’s more here than just architectural shock-and-awe to this hotel.

Best way to book: Book directly with Sofitel to earn and redeem Accor Live Limitless points. Select American Express cardholders can book via the American Express Hotel Collection and receive a few extras with their stay depending on the length, and same with Chase’s Luxury Hotel and Resort Collection for certain cardholders.

Sofitel may not have as much of a presence in the U.S. as it does elsewhere in the world, but its Chicago showing certainly makes a splash. That slanted facade is only part of it, as the chic public spaces exude cool for a hotel that tends to draw a more international and business-oriented crowd.

Rooms are a melange of cozy and sultry, with plush beds and paneled accent walls alongside leather seats and chaise lounges. Bathrooms are spacious and feature Balmain bath amenities. Nightly rates are also generally more affordable than similar high-end hotels closer to Michigan Avenue.

While hotel bars can always be fun, Sofitel’s Le Bar — this is a French brand, after all — is a particular highlight for those looking for a sleek spot to get a drink.

Rates at the Sofitel Chicago Magnificent Mile currently start at $175 per night.

Chicago Athletic Association The Unbound Collection by Hyatt

The Loop, Chicago, Illinois, USA

Best for: History lovers looking for a luxurious embrace of athleticism and Neo Gothic architecture (the convenience to Millenium Park is an added bonus)

Why stay here: No need to head to Venice. Cash in some of those World of Hyatt points burning a hole in your wallet (er…or app) and treat yourself to this historic, architectural gem that brings the charm of an old-school sporting club into the modern era.

Best way to book: Book directly through Hyatt or the hotel website to earn and redeem World of Hyatt points. Select American Express cardholders can book via the American Express Hotel Collection and receive a few extras with their stay depending on the length, while certain Chase cardholders can get elite-like perks booking through Chase’s Luxury Hotel and Resort Collection.

The Chicago Athletic Association name might have you thinking you’re heading into a fitness-focused hotel, and we hate to burst your bubble, but Pelotons won’t be the focal point here. Instead, it’s like stepping inside a super-exclusive private club (which it originally was when the establishment first opened in 1893).

The edifice’s original Venetian-inspired Neo-Gothic design is set to advantage indoors as well, where ornate stone fireplaces anchor plush seating vignettes. Sure, the athletic part kicks in, too: Old squash and fencing court flooring now panels the walls of the elevators, pummel horses serve as benches at the foot of guest room beds, and robes pay homage to what a boxer wears heading out to a prize fight.

Classic style reigns in guest rooms, ranging from brass-and-iron bed frames to clawfoot soaking tubs in select suites.

The playful design is reason enough to book a stay, but the Chicago Athletic Association also wins over guests with a variety of food and dining options — especially Cindy’s, a rooftop bar 13 stories up that overlooks Lake Michigan.

Rates at the Chicago Athletic Association are currently $157 per night.

Kimpton Gray Hotel

The Loop, Chicago, Illinois, USA

Best for: A comfortable, chic stay at a value in the Loop

Why stay here: Not every luxurious city hotel in Chicago has to come with sky-high rates. Plus, the decor and fashionable vibes here make it a preferred way to earn and redeem IHG One Rewards points when staying in Chicago.

Best way to book: Book directly with the hotel or IHG to earn and redeem IHG One Rewards points. Select American Express cardholders can book via the American Express Hotel Collection and receive a few extras with their stay depending on the length, and same for certain Chase cardholders through the Luxury Hotel and Resort Collection.

IHG One Rewards members looking for a high-end stay in downtown Chicago are fairly limited to a sole InterContinental on Michigan Avenue or two Kimpton properties. The Kimpton Gray Hotel wins out for its central location, strong design focus and overall comfort compared to its siblings.

While all guest rooms feature comfortable bedding, walk-in showers and city views, it might be worth considering an upgrade to a suite. These higher-end accommodations feature nicer (larger) bathrooms with soaking tubs and spa-like elements — sometimes a necessity while on a work trip.

The Kimpton Gray is a great option for travelers of all kinds, but it’s hard to shake the notion this is a hotel geared toward business travelers. Even the popular Vol. 39 bar and its library aesthetic scream Don Draper and a “Mad Men” after-work special. Hey, the drinks go down the same whether you’re there for business or leisure.

Rates at the Kimpton Gray currently start at $160 per night.

The Ritz-Carlton, Chicago

Gold Coast, Chicago, Illinois, USA

Best for: Expensable business travel with easy access to the Magnificent Mile and Lake Michigan.

Why stay here: The location at Water Tower Place just off Michigan Avenue tends to attract business travelers. But this is also one of the main luxury properties to earn and redeem Bonvoy points in downtown Chicago (at least until the St. Regis Chicago opens in 2023).

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits or directly via Marriott.

Along with the Park Hyatt, the Ritz-Carlton, Chicago, has a case for being one of the best luxury business hotels in the city. Don’t rule this hotel out if you’re coming just to sightsee, though. The Ritz is on the block between Michigan Avenue and the Museum of Contemporary Art Chicago and only steps away from the 360 Chicago observation deck at 875 North Michigan Avenue (better known as the John Hancock Center until 2018).

Some of the similarity with the Park Hyatt continues with guest rooms, as both hotels feature an aesthetic of earth tones, light wooden furnishings and spacious bathrooms. The Ritz-Carlton wins out for better views — it is a few blocks closer to Lake Michigan, after all.

While “location, location, location” might be one of the best assets of the hotel, the glamorous feel throughout the hotel is certainly nothing to overlook. The Ritz-Carlton Spa offers a variety of treatments to unwind, while the hotel gym’s views over Lake Michigan should help inspire anyone to hit a personal record on the treadmill.

Torali is the Ritz’s Italian-focused restaurant that also includes a bar and rooftop lounge of the same name; though, morning coffee at The Cafe — a glassed-in setting with a greenhouse-like vibe — can feel just as fabulous.

Rates at the Ritz-Carlton, Chicago, currently start at $509 per night.

Thompson Chicago

Gold Coast, Chicago, Illinois, USA

Best for: Luxury travelers looking for homey touches and easy access to Lake Michigan running trails and other local venues.

Why stay here: You’re looking for a neighborhood feel to your stay and want easy access to the Loop — without actually staying in the Loop.

Best way to book: Book directly with Hyatt or the hotel website to earn and redeem World of Hyatt points, or through the Chase Luxury Hotel and Resort Collection to enjoy elite-like benefits.

The Thompson Chicago represents a stay in the heart of the city without feeling so sterile or standardized as a major chain hotel (even though it is part of World of Hyatt). The room designs skew masculine with a mix of dark frames and creamy wall colors. Pillow lovers can rejoice, as there is an abundance of those to make dreams even sweeter when you finally get to curl up in bed.

It’s easy to splurge and spend more for a room or suite with a balcony or a better view of Lake Michigan and the surrounding skyline. You also won’t have to go far for good food: Nico Osteria off the Thompson’s lobby is a beloved local staple for Italian seafood.

If you’re dining elsewhere, save time for a glass of something delightful at Salone Nico, a wine and cocktail lounge with velvet furniture galore that feels like something the “Sex and the City” girls would have patronized.

Rates at the Thompson Chicago currently start at $189 per night.

Soho House Chicago

West Loop, Chicago, Illinois, USA

Best for: Those looking to live like a member — even if just for a night — of one of Chicago’s most exclusive clubs for creatives.

Why stay here: You’ve always wanted to be a member of Soho House but don’t feel like being the 85,000th person on the wait list. Experience the club without the recurring monthly membership fee.

Best way to book: Book directly through Soho House’s website. Please note that non-members are charged an additional $130 for a Soho Friends membership to greenlight your room stay.

Soho House Chicago, like others in the Soho House network, isn’t the easiest place to get into. For starters, you have to be a member, and the wait list to even be considered to join is as hefty as it’s ever been. But there is a hack: Just book a stay in a Soho House guest room, and you can at least live like a member for a night or two.

Indulge in Soho House’s variety of restaurants, like Cecconi’s Roof Bar for Italian or dabble in Friday or Saturday afternoon tea service at the lobby bar. There’s even a health club equipped with cardio equipment and strength training, and personal trainers available. Steam rooms and lounges await after all that hard work.

Rates at Soho House Chicago currently start at $425 per night (and then tack on the additional $130 Soho Friends fee) for non-members.

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

River North, Chicago, Illinois, USA

Best for: Old-school luxury and design with a Michigan Avenue location that draws high-end business travelers.

Why stay here: Perhaps you’re feeling like something a little more unique and bespoke than one of Marriott’s core top-end brands like the nearby Ritz-Carlton.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits or directly via Marriott. Select American Express cardholders can book via the American Express Hotel Collection and receive a few extras with their stay depending on the length, and certain cardholders can book through Chase’s Luxury Hotel and Resort Collection for elite-like perks.

Sumptuous interior design, a central location in the heart of the Magnificent Mile and an overall posh feel make a stay at The Gwen feel like you’re in Windy City high society. Housed in the historic art deco McGraw-Hill Building, the Gwen is a jewel in Marriott’s Luxury Collection of design-focused hotels.

A luxe rooftop terrace overlooks Michigan Avenue with a peek at Lake Michigan. The Gwen even offers a glamping package for those looking to sleep under the stars on the terrace. Otherwise, Upstairs at the Gwen offers terrace cocktails — from a chilled white wine in the summer to warm drinks served among the fire pits during chillier weather.

The Gwen’s 311 guest rooms and suites are tastefully appointed with a mix of sleek bedding in gray and other earth tones as well as Frette linens. Suites are an indulgent upgrade at the Gwen, as some feature terraces — the Gwen Lux Suite’s terrace can accommodate a whopping 50 guests — and others are just tranquil spots to take in city views over the Magnificent Mile.

Rates at The Gwen currently start at $224 per night.

Virgin Hotels Chicago

The Loop, Chicago, Illinois, USA

Best for: Trendy, youthful vibes at a value in the heart of the Loop.

Why stay here: You want to experience a little bit of everything: Millennium Park, theaters, restaurants, Michigan Avenue shopping, etc. The Virgin Hotel Chicago is where it all convenes in downtown Chicago — and rooms are affordably priced compared to others on this list.

Best way to book: Book through our partner Skylark to enjoy elite-like benefits and on-property credits or directly via Virgin Hotels. Select American Express cardholders can book via the American Express Hotel Collection and receive a few extras with their stay depending on the length, while certain Chase cardholders can book it through the Chase Luxury Hotel and Resort Collection. Virgin’s Virgin Red loyalty program is also a transfer partner with Capital One.

The Virgin Hotel Chicago is where you go for an un-stuffy stay in the heart of downtown Chicago. The crowd skews younger, but how could it not with its driving decor theme of deep red and embrace of bar-forward fun?

Guest rooms are standard Virgin Hotels fare: clean, modern and sleek, with comfortable beds hugged by a creamy leather headboard and footboard that beg you to spend the morning working in your bathrobe. Bathrooms include well-lit dressing areas and often feature privacy doors to cordon them off from the bedroom.

Cerise, the Virgin’s rooftop cocktail lounge, is highly popular in the summer but also features a holiday pop-up in the winter to keep folks coming in during Chicago’s colder months. For those sticking closer to ground level, Miss Ricky’s offers a popular brunch that seems like the perfect place to recap the prior night out on the town.

Rates at the Virgin Hotel Chicago currently start at $159 per night.