What are the best places to stay in Chicago?

©Waldorf Astoria Chicago

Don't be surprised if the Five-Star Four Seasons Hotel Chicago has a file on you. The staff meets every morning to go over who's arriving that day and what they might need, whether it's something you requested prior to your visit or something they know by scrolling through their huge database of guests. It's this flawless service that makes a stay here feel exquisitely relaxing. It also doesn't hurt that the hotel recently underwent a thorough revamp, and is just steps from the city's best shopping.

Steps away is the Five-Star Peninsula Chicago, which mixes Old World opulence with Asian-influenced style. The hotel's graceful service befits the dignified atmosphere of this gem. But the Peninsula's crown jewels are also its most delicious. The trendy Shanghai Terrace serves Asian-inspired fare and cocktails, Pierrot Gourmet is a sunny morning spot to start the day with breakfast and brunch and a late-night room service order of a famous Chicago-style hot dog is practically mandatory during any Windy City visit.

You might be confused when you walk into Five-Star Trump International Hotel & Tower. Is it a hotel? Is it a condo building? It's both, and the understated but upscale lobby is a precursor to everything this well-done hotel has to offer: A sophisticated but relaxed lounge; a gorgeous, Five-Star fine dining restaurant, Sixteen; lavish rooms where every detail has been taken into consideration (down to Sub-zero refrigerators); and amazing views from everywhere.

Located high atop Water Tower Place along Michigan Avenue, Four-Star The Ritz-Carlton Chicago underwent a major renovation in 2010, giving rooms a sophisticated and modern makeover. The Deca restaurant on the 12th floor is a chic place for cocktails and bistro fare.

The Four-Star Waldorf Astoria Chicago is adorned with chandeliers inspired by Coco Chanel's jewelry and features only 10 rooms per floor, which include fireplaces, terraces, and white Carrera marble bathrooms. The elegant Parisian-style building has a cobblestone motor court, a Greek-columned spa, handsome bar and two fantastic restaurants.

With its cherry-wood design and gold and mocha accents, the Four-Star Park Hyatt Chicago is a prime choice for a striking stay in Chicago. Anything you could need is a question away with the hotel's butler service and oversized tubs and room views of the Windy City's famous skyline and Lake Michigan guarantee your a fair share of relaxation and beauty during your stay.

  • On July 29, 2013
    Lauren Viera answered the question: Lauren Viera

    What are the best winter activities in Chicago?

    So many! Instead of shutting down, like most towns with a cold snap tend to do, Chicago embraces its long winter with seasonally appropriate activities. The classic winter activity, ice skating, takes place all over town, from downtown’s McCormick Tribune Plaza and Ice Rink, to Hyde Park’s Midway Plaisance Park. A few more details on ice skating in Chicago can be found here.

    Leading up to the holidays, it’s fun to check out the window displays at Macy’s on State Street, which are always done to the nines. It’s just a few blocks from Millennium Park, which always has a lot of winter programming, including a whole month of candlelit Caroling at Cloud Gate (aka “The Bean”) on Friday evenings.

    Finally, ’tis the season for wrapping your hands around a mug of hot chocolate. The past few years, especially, have seen a massive surge in exotic and decadent hot chocolates, available at finer patisseries and restaurants around town. My favorite is the aptly named Mindy’s HotChocolate in Bucktown, where no less than five types of hot chocolate are on the menu year-round.
  • On July 29, 2013
    Lauren Viera answered the question: Lauren Viera

    What are the best fall activities in Chicago?

    One of my new favorite early fall traditions has only been around for a few years, but it’s a fun way to kick off the season. It’s called Design Harvest, a kind of open-house for all of the interiors and design retailers that comprise the Grand Avenue Corridor in West Town. There are hayrides and cider, harvest-style beer and even live bands with a knack for hootin’ and hollerin’ along. It’s a lively little festival that I imagine will grow in the coming years.
  • On July 29, 2013
    Lauren Viera answered the question: Lauren Viera

    What are the best summer activities in Chicago?

    One of my favorite summer activities is to float down the river at a leisurely pace, courtesy of the Chicago Architecture Foundation's architectural boat tour, which runs during the warm months. The 90-minute tour takes you through the heart of the city via the Chicago River, with unparalleled, up-close views of the skyscrapers.

    My other favorite summer activity doesn’t require any tickets: pack a picnic (or just pick up a few provisions at any of the downtown delis) and spread a blanket on the lawn at Millennium Park for the series of free concerts taking place all summer. From classical performances by the Grant Park Music Festival to indie rock and jazz via the Downtown Sound and World Class Jazz series, there’s always something fun on the lawn.
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    Kevin Aeh
  • On July 23, 2013
    Kevin Aeh answered the question: Kevin Aeh

    Where is the best shopping in Chicago?

    Of course, Michigan Avenue is a must-visit. The shopping street, dubbed the "Magnificent Mile" offers just about every major store from the Apple Store to Top Shop/Top Man and Nordstrom to Neiman Marcus. Just around the corner from Michigan Avenue is the Gold Coast neighborhood, which offers spendier designer names and stores (think Barneys, Prada and Tom Ford) and a few local shops like the trendy women's boutique Sofia.

    Bucktown is another great spot to find designer boutiques: Marc by Marc Jacobs, Cynthia Rowley and more. The hood also offers great indie shops such as upscale men's store Apartment Number 9, Roslyn (a great women's boutique) and Virtu (a nice spot for gifts).

    If you're looking for items for the home, head to Andersonville. The northside 'hood has become the city's unofficial home decor district, filled with great antique and vintage decor shops with a heavy focus on Mid-Century Modern looks. Standout shops in the area include Room Service, Scout and Brimfield.
  • On July 22, 2013
    Kevin Aeh answered the question: Kevin Aeh

    What are the best activities to do in Chicago?

    If it's summer in the city, you have to find a way to get on a boat. Chicago's skyline is especially majestic when viewed from out on Lake Michigan. Luckily, there are a few easy ways to get out on the water. Navy Pier offers a number of boating options, from dinner cruises to speed boat tours. (FYI: That's also where you'll view an impressive fireworks show on Wednesday and Saturday nights.) The Chicago Architecture Foundation boat tours take you through Chicago's river, where you'll get new views (and some background info) on some of the city's most famous buildings.

    Bike riding is becoming more popular in Chicago. Proof: Divvy Bikes recently set-up a bike-sharing program throughout the city, where you can rent a bike for the day and pick it up at any docking station. Riding a bike along the lakefront path is also a great way to see Chicago like a local. 

    Chicago also has a great theater community, and if you have time to see a show, I'd definitely recommend it. There's always Second City, The Goodman and Steppenwolf as well as the many storefront theaters located throughout the city. Many famous actors (including Tina Fey, John Malkovich, John C. Reilly and more) got their starts on Chicago stages, so chances are you'll catch a performance from the next big thing. 
  • On July 16, 2013
    Kevin Aeh answered the question: Kevin Aeh

    What are the best attractions in Chicago?

    Any Chicagoan will tell you that Millennium Park is a must-visit. During the summer, I'll attend the free concerts at the Jay Pritzker Pavilion at least three or four times. The concerts (everything from jazz to classical and indie to even some electronica) are held on various nights throughout the week and provide the perfect background for a picnic and a bottle of wine. While you're at the park, you have to take a picture of your reflection in front of “The Bean"—Anish Kapoor's massive mirrored Cloud Gate sculpture that resembles a giant kidney bean. And in the winter, you can ice skate in the park.

    Some might argue that the top of the John Hancock Building is a bit of a tourist trap, but the views are pretty awesome. I say pop-in for a drink in the Signature Lounge on the 96th floor. The drinks are slightly overpriced, but the views are worth it. I've also heard there's a great window view from the women's restroom—but, of course, haven't seen it for myself.
  • On July 1, 2013
    Lauren Viera answered the question: Lauren Viera

    What are the best markets in Chicago?

    Perhaps Chicago’s best known high-end market is Fox & Obel, specializing in artisan baked goods, rare preserves and treats, and incredible produce, as well as an impressive prepared-foods section. There’s a bistro here, too, serving a full menu of items for breakfast, lunch, and dinner.

    I’m also a fan of the Mariano’s chain, which is more of a full-service grocery store, but with impressive prepared-foods and deli sections. The downtown location, adjacent to Millennium Park, is a popular stop for picnickers heading to al fresco concerts in the park.

    With four locations in the city, The Goddess and Grocer is a popular specialty market worth popping into for local provisions and treats. I love that there’s always a selection of Vosges Haut Chocolat, a must-eat souvenir.
  • On July 1, 2013
    Lauren Viera answered the question: Lauren Viera

    What are the best places for breakfast in Chicago?

    Chicago is a brunch town, with nearly every restaurant worth its salt offering late-morning options on Sunday, or both weekend days. Breakfast, on the other hand, is more rare, but there are plenty of recommendable options.

    One of my favorites is Lula Café in Logan Square, which has been a popular neighborhood restaurant for more than a decade. There are a half-dozen standard entrees on the menu and a half-dozen more specials that rotate daily. Bin 36, best known for its wine-paired dinner entrees, is a solid River North option for both business professionals and tourists staying in this hotel-heavy ’hood. Ann Sather’s quartet of Swedish-inspired restaurants open early for breakfast every day of the week, and the sweet smell of cinnamon rolls beckons visitors from outside the doors. Rick Bayless’s Xoco is another River North option, serving modern-flaired Mexican breakfast (tortas, empanads) until 10 a.m.
  • On July 1, 2013
    Lauren Viera answered the question: Lauren Viera

    Where is the best Chicago nightlife?

    Chicago is a big enough city that there are multiple neighborhoods with great nightlife. It all depends on what you’re in the mood for, how much you’re willing to spend, and how late you want to stay out.

    If you’re going all out, River North is the city’s best club-centric destination. Home to popular bottle-service destinations such as Studio Paris, this is the it neighborhood to see and be seen. Countless bars and lounges ring this neighborhood that comes to life at night, and many stay open until 2 a.m. on weekdays, and 3 a.m. Saturdays.

    Personally, I’d much rather bar-hop in Wicker Park, Chicago’s one-time artists’ neighborhood that’s now home to some of the best cocktails and bar-bites in town. There’s always a good time to be had at rowdy Big Star, located in the heart of this hip neighborhood, and just across the street is The Violet Hour, a demure, hushed haven for excellent drinks in the dark.

    Sports fans usually gravitate toward Wrigleyville to celebrate post-game at destinations such as John Barleycorn and the Cubby Bear. Fair warning: If you’re a White Sox fan, you’re bound to be outnumbered in this party zone in the shadow of Wrigley Field.
  • On July 1, 2013
    Lauren Viera answered the question: Lauren Viera

    Where are the best places to hear live music in Chicago?

    As the home of Chess Records, the famous mid-century R&B and blues label that had a partnership with Memphis’ Sun Studio, Chicago has a long history with southern-rooted music. But meanwhile it’s developed an eclectic style all its own, thanks to thriving scenes fostering everything from jazz to metal. As someone who plays in a local band, I’m always impressed with how many active musicians there are in Chicago, and how many places there are to catch live music on any given night of the week.

    My go-to is the Empty Bottle in the Ukrainian Village in the West Town neighborhood. Established more than two decades ago, it’s a small rock club with a world-class reputation for debuting up-and-coming artists, and it’s one of the best venues to hear successful local bands, and is especially popular on Free Mondays.

    For jazz, the Green Mill is an iconic classic. Anchoring the Uptown neighborhood, this small room plays host to everything from be-bop to poetry slams, and there’s something on nearly every night of the week. Prepare for crowds on weekend nights.

    Another great club-sized venue is Schubas, in the Southport Corridor of Lincoln Park. This is one of the best-sounding rooms in town, and hosts an exciting cross-section of talent, from internationally touring indie rock acts to burgeoning local songwriters and DJs. There’s a great pub and restaurant here, too.

    Perhaps Chicago’s best known large concert venue is The Metro, which recently celebrated its 30th anniversary. America’s most famous rock bands have all made stops here, from Nirvana to the Smashing Pumpkins, and the two-story space continues to host must-sees on a nightly basis.

    For those who enjoy intimate concerts with room to sit and enjoy a cocktail, check the calendar at the luxe Mayne Stage. A century-old building previously known as the Morse Theatre, the venue was rebranded in 2008 and now features top-of-the-line sound and lighting, sight-lines and amenities such as plush booth cabaret seating.