Chicago Luxury

From fancy hotels to fine dining, the city of Chicago is your (very expensive) oyster. But before you and your money part ways, you should know what's worth it and what's not. Here are some of the most worthwhile spots to splurge in town. 
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1723 North Halsted St., Chicago, IL 60614

At Alinea, eating is about more than food, it's an event. Chicago's only 3-Michelin starred restaurant serves up gastronomic surprises (think: a green apple taffy dessert infused with helium to make an edible balloon) that have people booking flights to the Windy City for the sole purpose of eating here.

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Next Restaurant

953 W Fulton Market, Chicago, IL 60607

From the minds behind Chicago's only 3 Michelin-starred restaurant, Alinea, comes Next. The concept here is ever changing, with new menus introduced every three months (past menus include Paris 1909 and Childhood). Rather than making reservations, diners have to buy tickets beforehand, like they're going to a show (and actually, it kind of is one).

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Hilton Chicago

720 S Michigan Ave, Chicago, IL 60605

While this hotel has rooms as low as $79/night, it also is home to the most expensive hotel suite in the Midwest. Refurbished in 2013, the Conrad Hilton Suite spans 5,000 square feet over two floors, and costs about $10,000 a night. Guests able and willing to pay up are rewarded with an en suite baby grand piano, pool table and a helipad.

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The James Chicago

55 E Ontario St, Chicago, IL 60611

The James serves up modern luxury with all the amenities. Rooms are spacious (by downtown hotel standards), with city views and complimentary WiFi. The hotel is also home to David Burke's Primehouse, named the city's best steakhouse by Chicago Magazine. For smaller bites, head to the newly opened Burke's Bacon Bar, which serves up pork-centric sandwiches. For late night sips, head to the hotel's new cocktail bar, which is already attracting a trendy crowd.

The Magnificent Mile

625 North Michigan Avenue, Suite 401 Chicago, IL 60611

New York has 5th Avenue. LA has Rodeo Drive. Chicago has the Mag Mile. Those with money to spend will have plenty of choices, with shops like Burberry, Armani and Tiffany's lining the street. Start at the Old Water Tower building then work your way south towards the river. Once you've shopped your heart out, you can take a well deserved break in Millennium Park.

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Architecture River Cruise

Chicago, IL 60601

Home of the skyscraper, taking the time to appreciate the city's architecture is a major thing to do when you're in town. There are a lot of boat tours to choose from, but your money is best spent on the slightly more expensive tour run by the Chicago Architecture Foundation. With experienced, knowledgable staff, you'll walk away tons of fun facts and a deeper appreciation of the city.

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15 East Huron Street Chicago, Illinois 60611

When you're looking for the perfect cocktail dress (and money is no object) Ikram is your store. With a selection of carefully curated clothes from the world's top designers, Ikram has long been a magnet for chic shoppers and celebrities (the store is actually a favorite of the always impeccably-dressed Michelle Obama). If you manage to work up an appetite while browsing, head upstairs to the cafe, where sandwiches and salads are surprisingly affordable, given the setting.

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3201 W Armitage Ave, Chicago, IL 60647

This trendy speakeasy-style bar has quickly shot to the top of everybody's list of places to drink in Chicago. Choose a cocktail from the gin-centric menu, then relax by one of the two fireplaces. Stick around until midnight, when they pass out complementary chocolate chip cookies.

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Intelligentsia Coffee

3123 N Broadway St, Chicago, IL 60657

If Intelligentsia feels a little pretentious, that's because it is. But, it's well worth queuing up behind the bespectacled, bearded and tattooed patrons to grab a cup of joe at this Chicago-born institution. I don't know if it's because Chicago suffers from such harsh winters, but they really know how to brew a cup. Take some time to read the descriptions of each roast before ordering, then taste it first before adding any sugar or milk to ensure you can really appreciate the flavor (and in case you're reading this and feeling a bit skeptical—trust me, this is far from Folger's).

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980 N Michigan Ave #2, Chicago, IL 60611

If you were to make a bucket list of Chicago restaurant to eat at before you die, Spiaggia should definitely make the cut. Pillowy gnocchi, rich sauces and earthy truffles adorning nearly everything, it's not hard to see why this is considered one of the best Italian restaurants in the country. Spiaggia has even gotten the attention of the rich and famous, and is one of the Obama's favorite date night spots.

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Raffaello Hotel

201 East Delaware Place, Chicago, IL 60611

Location, amenities, and a killer bar—the Raffaello has it all. This place drips with luxury, from the grand red brick building to the marble lobby to the in-room personal shoeshine machines. And even though the hotel is located literally next door to the John Hancock Center and the Mag Mile, the truth is you don't even need to leave the building to get a taste of some of the best of Chicago—try some of the city's top doughnuts at the Glazed and Infused located right in the lobby, or head up to the 18th floor to Drumbar, consistently recognized as one of the best bars in Chicago.

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Directly linked to the North Bridge shopping center (with 50 stores, a Nordstrom, and 20 restaurants), you don't even need to step outside to shop Michigan Avenue, which is a serious perk during the harsh Chicago winters. Rooms are nicely sized, decorated in a neutral palette of whites and tans. The hotel offers free WiFi, a rarity for upscale lodging, and complimentary access to a recently refreshed gym. The Conrad does have a restaurant and a convenience store (with an ATM) in the lobby, but the neighborhood and aforementioned mall attached to the hotel provide lots of options.

Last updated at Mar 30, 2015