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The Only Guide to Traveling to Chicago With a Group Is Here & It's Good

photo: Nick Murway

Summertime always reminds us of Chicago, a place that’s absolutely buzzing with energy this time of year. Lately, we’ve been hearing about all kinds of new hotels and restaurants in the city, but we also want to share some of our old faithfuls with you. Here, we’re diving into boutique hotels and luxury high rises alike. We’re exploring Michelin-starred restaurants and letting you in on the best Korean-American restaurant around. We’re also sharing some of our favorite Chicago cocktails, from those infused with CBD to a green chile bramble. So, come along as we wander around the Windy City.

Reporter: Alyssa Brown

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There’s certainly no shortage of hotels in Chicago, but when it comes to boutique luxury and designer digs, here are some of our favorite places to stay in the Windy City. Of course, every neighborhood in this city has its own personality, and these hotels reflect the best of each.
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Freehand Chicago

River North, Chicago, Illinois
River North sets the scene for this laidback boutique hotel with 1920s Art Deco roots and a modern Midwestern vibe. The options for group stays at Freehand are legit, ranging from a quad room with four twin-sized bunk beds to a two-bedroom penthouse with a cozy living room.
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Ace Hotel Chicago

West Loop, Chicago, Illinois
Set in West Loop’s Fulton Market, Ace Hotel Chicago includes 159 signature Ace-style boutique hotel rooms. As far as hangout spots go, there’s a spacious rooftop lounge and an all-day restaurant called City Mouse, which is run with the team from local hotspot Giant.
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The Hoxton, Chicago

West Loop, Chicago, Illinois
This designer boutique has 182 rooms filled with leather furnishings, mid-century style and rad wallpaper. The Hoxton is set in the heart of Fulton Market District, an area known for its galleries, boutiques and proximity to Restaurant Row.
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Loews Chicago Hotel

Streeterville, Chicago, Illinois
Set in the heart of Chicago’s Streeterville neighborhood, this downtown hotel combines luxurious contemporary guest rooms, delightful dining spaces and a very nice spa. If you’re looking for an all-around good time, this hotel may be your best bet.

The Gwen, a Luxury Collection Hotel

Downtown, Chicago, Illinois
Ever considered urban glamping? Chicago would be a great place to do it, especially if it means waking up on the 16th-story rooftop of this glamorous hotel overlooking the Magnificent Mile. Through September, The Gwen offers a VIP glamping experience that includes airport transfers, a welcome bite and fancy gold-leaf s’mores.
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The Robey

Wicker Park, Chicago, Illinois
The Northwest Tower in Wicker Park is an Art Deco beaut that dates back to 1929 and has recently been transformed into a modern 89-room hotel known as The Robey. The suites here have a minimalist feel, while the shared spaces are gorgeous and glam as could be. Hot tip: For those planning a wild night out in Chicago, the rooftop lounge at The Robey is an awesome place to have a nightcap before heading to your suite.

Hotel EMC2, Autograph Collection

Streeterville, Chicago, Illinois
Science, art and luxury collide at this Autograph Collection hotel in the heart of downtown. The rooms here are divine, the location is central and the restaurant brings science and art right along to the dinner table.

LondonHouse Chicago, Curio Collection by Hilton

Downtown, Chicago, Illinois
The spacious suites at LondonHouse come with incredible views of the Chicago River, Magnificent Mile and Lake Michigan. The luxury hotel is huge, with 452 rooms, and there’s an awesome rooftop bar that makes a great late-night hang spot.
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St. Jane Chicago

Downtown, Chicago, Illinois
Jazzy, plush and modern, the St. Jane Hotel in the landmark 1929 Art Deco Carbide and Carbon building is a bold addition to the cool Chicago hotel scene. The rooms here look like they belong in the pages of a design magazine, while the Jamaican cocktail lounge and American brasserie provide rad gathering spots when you’re meeting up with local friends.

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If we had to come up with one, and only one, thing that makes Chicago an all-star city, it would absolutely be the culinary and cocktail scene. In 2018 alone, there were 27 Michelin stars awarded to 22 of the city’s restaurants. Beyond the award-winning spots, there are plenty of casual hangouts, rooftop bars, barbecue joints and so much more.
Photo:Matt Haas
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Maddon’s Post

Lake View, Chicago, Illinois
Wrigleyville is home to this Italian-Polish restaurant from multiple James Beard Award-winning chef Tony Mantuano and Cubs Manager Joe Maddon. Maddon’s Post is an all-day dining spot that serves everything from wood-fired pizzas to pierogies, lambrusco to Okocim. If you’re in the mood for an authentic Chicago atmosphere, head to this spot and sit outside to take it all in.
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Bellemore

West Loop, Chicago, Illinois
Artistic American is the predominant theme at Bellemore, exhibited both on the plates and in the atmosphere. You can expect to dine on a well-rounded dishes here, as the award-winning chef sees style, art and technique as vital components of a great meal.
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Cindy'slearn more

Set thirteen stories above Chicago’s famous Millenium Park, the rooftop at Chicago Athletic Association is one of the best sunset viewing spots in the city. Cindy’s has a buzzy energy, and serves up delicious cocktails, a solid offering of organic wines and American bistro-style fare.
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Café Cancale

Wicker Park, Chicago, Illinois
This new Wicker Park seafood restaurant is named after the small French coastal village. Cancale isn’t a typical grab-n-go café, but is instead a place to indulge on oysters, clams, whole grilled lobsters and steak frites. It’s also a place with a killer happy hour – think dollar oysters and seven-dollar martinis.
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Young American

Logan Square, Chicago, Illinois
This new Logan Square hangout is quickly becoming known for its cocktails and signature goth bread with activated charcoal, leek ash, nighttime cheese, smudge butter and yolk. The vibe here is relaxed, friendly and all sorts of lit up with neon lights.

Big Star

Wicker Park, Chicago, Illinois
If your ideal Wicker Park afternoon includes hanging out in the sunshine while noshing on queso, guac and tacos, Big Star is sure to be on your Chicago hit list. As a neighborhood go-to, the place has energy in abundance. Lest we forget to mention the numero uno highlight: Palomas are served by the pitcher here!
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Parachute

Avondale, Chicago, Illinois
Michelin-starred Korean-American fare is served in a warm, comfortable 40-seat space at Parachute. This restaurant gets all the glory and fanfare it deserves, while serving some of the best food you’ll find in this city. 
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Aba

West Loop, Chicago, Illinois
A Mediterranean-meets-Californian restaurant with a gorgeous rooftop in West Loop, Aba’s signature dishes include chrispy short rib hummus and skirt steak shawarma. Local cocktail queen Liz Pearce leads the cocktail program, which currently includes a green chile bramble with St. George green chile, Leopld blackberry, lemon and honey.
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Alinea

Lincoln Park, Chicago, Illinois
With a whopping three Michelin stars, Alinea is consistently recognized as one of the best restaurants in Chicago. So, what does it mean to dine at the top? For starters, your menu might include 10-12 or 14-16 courses with or without beverage pairings. Or, if you’re feeling particularly VIP, you can actually book a seat at the kitchen table and have a fully private, immersive dining experience with up to 6 guests.
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Pacific Standard Time

River North, Chicago, Illinois
West Coast cooking meets Midwest hospitality at River North’s Pacific Standard Time, a restaurant focused on bringing wood-fired flavors to the Chicago masses. This hotspot has quickly garnered plenty of media attention since its fall 2018 opening, scoring multiple awards for its stunning design.
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Tied House

Lake View, Chicago, Illinois
Okay, tourists, this neighborhood gem is one you’re going to want to head to Lake View for. Tied House does dinner and weekend brunch in a gorgeous, modern space. Think biscuits and gravy, breakfast ramen or a pork pastrami melt for brunch, or venison tartare, grilled octopus or a roasted half chicken for dinner.
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The Publican

West Loop, Chicago, Illinois
It’s hard to miss the trifecta focus of this West Loop restaurant, which is all about oysters, pork and beer. Rustic, farmhouse fare highlights the best of local purveyors at The Publican, and the beer hall atmosphere is always warm and welcoming.
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Sawada Coffee

West Loop, Chicago, Illinois
Whether you’re in need of a caffeine fix or a boozy chai slow-down, Sawada offers a bright, industrial coffee shop with all the goods. And if you’re in desperate need of a sugar rush, the Doughnut Vault keeps this spot fully stocked with sweet treats.
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Maude's Liquor Bar

West Loop, Chicago, Illinois
With its warm lighting, vintage aesthetic and delicious drinks, a visit to Maude’s is sure to cure anything that ails ya. Of all the places in Chicago to cozy up to the bar and get the lowdown on the best drinks from the bartender, this spot may just be number one.
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Galit

Lincoln Park, Chicago, Illinois
Besides various types of hummus and accoutrement, Galit mostly serves fresh, flavorful Middle Eastern food that’s been cooked over coals. Located in Lincoln Park, this flavor haven is the brainchild of Andrés Clavero and James Beard Award-winning chef Zachary Engel.
Photo:Tim Bish
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Smoque BBQ

Irving Park, Chicago, Illinois
Brisket, pulled pork, Texas sausage and ribs. Yes, yes, yes and yes. This Irving Park barbecue joint takes their meat-by-the-pound seriously, and you’re gonna want in on this action. If you’re looking to cure a vacation hangover, you really can’t go wrong with any of the meats served with classic sides like mac-n-cheese with breadcrumbs, tangy coleslaw and peach cobbler.
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Pub Royale

Wicker Park, Chicago, Illinois
Wicker Park’s Pub Royale is probably best described as a cozy English pub that serves Indian food. It’s not the kind of place where you book a reservation, so just grab your travel buddies and rock up to this casual haunt.
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Chicago is one of the best American cities for enjoying public spaces and museums. Looking for the best shopping district? Head to the Magnificent Mile. Craving a little time spent on the water? Take a cruise on the Chicago River. Want to see what all the Millenium Park fuss is about? Head downtown.
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River Cruise with Chicago's First Lady Cruises

Downtown, Chicago, Illinois
For those who love architecture, or simply love being out on the water, Chicago’s First Lady Cruises offers a 90-minute tour of the city's most famous buildings and architectural styles. There’s a full-service bar on board too, so you can sip a nice glass of wine while brushing up on your knowledge of this incredible skyline and its history.
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The Art Institute of Chicagolearn more

Located in Grant Park, The Art Institute of Chicago has a wide-ranging collection that includes impressionist artworks, fashion and locally important works. Be sure to check what’s on while you’re in town, as the exhibitions and events are always changing. 
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The Field Museum

Downtown, Chicago, Illinois
Learning about science is made into a fun journey at The Field Museum, where visitors might spend their time soaking up the hidden lives and worlds of bugs or going on an underground adventure. You might even take a wander through the aquarium or planetarium while you’re here.
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Millennium Park & Grant Park

Downtown, Chicago, Illinois
Chicago’s parks each have their own thing going on, but the two most famous of the bunch are Millenium Park and Grant Park. Grant Park stretches over 300 acres on the lakefront in Chicago’s downtown area, and is home to Maggie Daley Park, Buckingham Fountain, the Art Institute of Chicago and the Museum Campus. Millenium Park is also part of Grant Park, and is the area that includes one of the city’s most famous works of public art, Anish Kapoor’s Cloud Gate. It’s impossible to miss this iconic destination during a trip to the Windy City, and you certainly wouldn’t want to.
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See a Game at Wrigley Field

Lake View, Chicago, Illinois
There’s no way to get an authentic Chicago experience without a trip to famous Wrigley Field! Check the calendar to see what games are playing while you’re in town and be sure to snag some local team gear before heading over.
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Shop the Magnificent Mile

Downtown, Chicago, Illinois
There are plenty of great shopping destinations in Chicago, but Magnificent Mile takes the cake for convenience and sheer volume. There are three vertical shopping malls here, including one that’s exclusively for luxury brands. If you prefer to shop in flagship stores and boutiques, wandering N. Michigan Avenue may be the way you choose to go.

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