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Destination of the Week: Chicago

by on April 27, 2012 · 14 comments

in Destination of the Week

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This time around, we’re sticking to a fantastic city in America’s heartland for our Destination of the Week: Chicago.

As the “Second City,” and presiding over the “fly over” section of the US, Chicago often gets short shrift compared to flashier destinations like LA, San Francisco, Miami and New York, but there is plenty to see, do and eat there, and May is a great time of year to visit and enjoy the mild spring weather before the summer heat sets in.

YOUR EXPERIENCES
Destination of the Week pieces are not meant to be comprehensive guides to destinations since we don’t have the time or funds to visit all these places in person and report back to you. Nor are they endorsements of all the hotels we mention. They are simply roundups of top destinations that we have specifically pinpointed for the opportunity they present to use your miles and points to get to and stay there. As always, we welcome your comments to help enrich the content here, provide opinions and first-hand experiences of these destinations.

WHAT TO DO
Chicago’s a great town for lovers of art and architecture. Anyone will tell you what a fantastic experience taking an architectural boat tour is as you spend a couple hours on the Chicago River learning about the city’s history of innovation. There are actually quite a few companies that offer them, so be sure to do your homework and choose the one that’s right for you, but Chicago Line Cruises has a sterling reputation and does 90-minute tours daily.

There are also plenty of stationary museums including the sprawling Art Institute—where you can relive a moment from Ferris Bueller by staring at Seurat’s La Grande Jatte—the Field Museum of Natural History, which currently has special exhibits on the T-Rex and Genghis Khan, as well as the world-class Shedd Aquarium (there’s a special exhibit on jelly fish at the moment), and the fascinating Museum of Science and Industry.

The Cloud Gate sculpture in Millennium Park by Anish Kapoor. Photo by wallyg.

If you’re there for baseball season, take in a White Sox game at White Sox Park or a Cubs game at Wrigley Field, or spend a day sightseeing from on high at the observation decks of the Willis Tower (formerly Sears) or the Hancock Tower and then have lunch and a stroll along Navy Pier with its carnival games and the Chicago Children’s Museum. Maybe have a wander through Millennium Park south of the river to eye yourself in Anish Kapoor’s huge mirrored sculpture titled Cloud Gate, or take in a musical performance in the evening at one of the outdoor venues.

Let’s not forget, Michigan Avenue is one of the country’s, if not the world’s, great shopping streets, and visitors can find flagships of all the major fashion brands here including Tiffany, Giorgio Armani, Sak’s Fifth Avenue, Coach and more, plus the city’s most famous store, Marshall Field’s along nearby State Street.

Michigan Avenue has world-class shopping.

Chicago is also home to some of the country’s most famous restaurants including what just might be the ultimate gourmet dining experience at chef Grant Achatz’s Alinea, as well as more downhome food (they’re using a lot of offal these days) at restaurants like Girl and the Goat. Check out Chicago Magazine’s “Best New Restaurants of 2011” list for ideas of where to eat while you’re in town including Bistronomic for un-fancy French food, Cumin for Indian and Nepalese cuisine, Due Lire for Italian home cooking and even hearty Dutch fare at Vincent.

Food, culture, shopping—what more do you need for a great getaway?

GETTING THERE
Chicago O’Hare is a major hub for both United and American airlines, meaning Star Alliance and Oneworld members have tons of options flying here, whether you’re arriving domestically or internationally.

O'Hare's famous Hall of Flags in Terminal 3.

If you’ve recently taken advantage of the BA Visa 100,000 Avios offer, you might be interested in using some of those Avios to get to Chicago aboard BA’s partner airline, American. The great thing about Avios’s distance-based formula is that you can redeem them for award flights at lower levels—especially for a central destination like Chicago. Whereas on other US legacy carriers, an itinerary from either San Diego or Washington DC would cost you 25,000 miles roundtrip in most cases, using Avios, you’d only need 20,000 miles from San Diego, or a measly 9,000 miles for a roundtrip flight from IAD-ORD. Not bad for a quick getaway!

JetBlue also flies to O’Hare, while Southwest flies to Midway airport, closer to the city.

HOTELS
All of the major chains are represented in this enormous city, so we’ve picked out a few properties from each to highlight.

The Business Class Lounge at the Radisson Blu Aqua.

Carlson
Radisson Blu Aqua Hotel Chicago: Opened just last November, this hotel is located on the first 18 floors of the 81-story Aqua tower, this hotel has 334 luxury guestrooms with flatscreen TV’s and balconies. They also offer business-class rooms with access to the Business Class lounge on the 17th floor offering complimentary breakfast and an evening reception. There are  indoor and outdoor pools, a Jacuzzi, sauna, steam room, fitness center, and game room in addition to an outdoor terrace. The hotel’s restaurant, Filini features modern Italian cuisine. Rates in May begin at $279 a night or 50,000 Gold Points.

The Drake Hotel's historic foyer.

Hilton
The Drake Hotel: Dating back to 1920 as one of the first Lake Michigan hotels in Chicago, this hotel has 537 rooms including 74 suites. There is also an executive lounge on the 11th floor serving complimentary breakfast, hors d’oeuvres, and canapés. All the rooms feature the Serenity Bed, 32-inch plasma TV’s, high-speed internet access and a choice between city or lake views. The hotel’s main restaurant is the Cape Cod Room serving fresh seafood. Other dining options include the Palm Court, Drake Bro’s or the legendary hotel bar, Coq d’Or. Rates in May start at $159 a night. This is a Category 7 Hilton property, meaning one free night costs 50,000 Hilton HHonors points.

Other Hilton options include the also-historic Palmer House, which is a Category 7 Hilton property, meaning one free night costs 50,000 Hilton HHonors points. There is also the Hilton Chicago (Hilton Category 7, 50,000 points) and the Waldorf Astoria Chicago  (70,000 points per night), which just took over and rebranded the Elysian Hotel.

A Park King Room at the Park Hyatt Chicago.

Hyatt
Park Hyatt Chicago: This hotel has 198 guestrooms including 13 suites. The rooms have 32-inch flatscreen HD televisions, iHome alarm clocks, walk-in showers, and marble bathrooms. There is a 7,000-square-foot health club and full-service NoMI Spa as well as a 25-yard pool and whirlpool. There are window seats in the rooms to take in the lake or city views.  The hotel’s upscale restaurant is the NoMI Kitchen, serving contemporary American cuisine with French influences. The lowest rate we could find in May was $455 for a Park King Room. This is a Category 6 hotel, so free night redemptions require 22,000 Gold Passport points for standard rooms and 33,000 for suites. Also, the New Chase Hyatt Visa now gives two free award nights after your first purchase and if you’re already a Platinum member when you sign up, you also get two suite upgrade certificates to use on paid stays up to 7 days, and Diamond members receive their two free award nights in a confirmed suite.

There is also the Hyatt Regency Chicago which is a Category 4 hotel requiring 15,000 Gold Passport points.

A guestroom at the JW Marriott Chicago.

Marriott
JW Marriott Chicago: This 610-room hotel recently underwent a $396-million restoration. Rooms start at 445 square feet and have high ceilings, 42-inch LCD televisions, iPod docking stations and WiFi. There is also an executive floor with an executive club lounge open during the week. There is a 20,000-square-foot spa and wellness center. The hotel is home to The Florentine, which is part of the BLT restaurant group, serving Italian fare. Rates in May begin at $249 a night. This is a Marriott Category 7 property, and requires 35,000 Marriott Rewards Points (30,000 with PointSavers) for a free-night redemption.

There is also the Renaissance Blackstone Chicago Hotel (Marriott Category 6, 30,000 points), which is located near Grant Park and the Chicago South Loop as well as the Renaissance Chicago Downtown Hotel (Marriott Category 7, 35,000 points), which is located on the North end of the Loop. Other Marriott properties include the Chicago Marriott Downtown Magnificent Mile (Marriott Category 7, 35,000 points) and the Courtyard Chicago Downtown/River North (Marriott Category 5, 25,000 points).

Priority Club
There are actually 42 Priority Club properties around the city and its environs, so we’ll just cover a couple here.

A bright guest room at the Hotel Indigo.

Hotel Indigo: The young, hip brand in IHG’s portfolio, Hotel Indigo properties are known for cheery atmospheres and fun perks like iPads for guest use, cool bars and events, free breakfast and free in-room WiFi and more. This hotel is actually in the quieter Gold Coast area north of downtown, but still close. It has 165 guest rooms, the Golden Bean restaurant and the Phi Lounge open in the evening for cocktails and light bites, as well as an onsite fitness center. Rates in May start at $225 or 35,000 Priority Club points.

The indoor pool at the Intercontinental Chicago. The building was originally a 1920's athletic club.

Intercontinental Chicago: The Intercontinental Chicago is a grand old property right on Michigan Avenue in the middle of Chicago’s Magnificent Mile. The hotel is in a historic building originally constructed in 1929 as the Medinah Athletic Club. It has been an Intercontinental since 1988. The 792 rooms at this property were recently refurbished, though they still look kind of old-school with lots of plush fabrics in rich colors as well as heavy wooden furniture. Definitely not a contemporary look. The hotel has three restaurants and bars: Michael Jordan’s Steakhouse, The Continental for breakfast and brunch, and ENO for wine, cheese and chocolate, as well as a Starbucks. Other amenities include a newly equipped fitness center and a business center. Rates in May start at $219 or 50,000 Priority Club points.

In addition to these two properties, there are also two Crowne Plazas downtown, several Holiday Inns and Holiday Inn Expresses, Candlewood Suites and Staybridge Suites. TPG also had a great experience staying out at the Intercontinental O’Hare, which he said was one of the nicest hotel airports he’s ever been to.

The whimsical lobby at the W City Center.

Starwood
W Chicago City Center: Located in the middle of the Chicago Loop, this 368-room hotel is close to the Sears Tower, Chicago Art Institute, Millennium Park, as well at the theatre district. All rooms and suites feature W’s hotel pillowtop mattress with feather bed, 42-inch plasma televisions and marble bathrooms with Bliss bathroom amenities. The hotel has a SWEAT fitness center, Wired business center, and complimentary Acura car service. Dining options include the Lobby Bar, as well as IPO, serving Urban American cuisine in a casual setting.  Rates in May start at $219 per night or 12,000 SPG points as this a category 5 SPG hotel.

The Westin Michigan Avenue.

The Westin Michigan Avenue Chicago: Located on Michigan Avenue near Water Tower Place, this hotel has 752 guest rooms including 23 suites. Rooms feature 37-inch flatscreen televisions, in-room internet, Westin Heavenly Beds and Heavenly Baths with dual showerheads, and marble countertops. The hotel also has a WestinWORKOUT fitness center and Body Rituals Boutique Spa. The hotel’s restaurant is The Grill on the Alley serving American cuisine for breakfast, lunch and dinner. Because of the limited number of suites in comparison to the hotel number of rooms, it might be worth using SPG Suite Night Awards during your stay of you are a SPG Platinum member. Rates in May start at $179 per night or 12,000 SPG points as this a category 5 SPG hotel. Cash and points is also available for 4,800 points and $90.

Other Starwood properties in Chicago include The Westin Chicago River North (SPG Category 5, 12,000-16,000 points) and The Sheraton Chicago Hotel & Towers (SPG Category 4, 10,000 points) both of which feature club floors with free access for SPG Platinum members. There is also the Four Points by Sheraton Chicago (SPG Category 3, 7,000 points), and the other W Chicago – Lakeshore, which offers views of Lake Michigan (SPG Category 5, 12,000-16,000 points) and features the only Bliss Spa in Chicago.

Other Options
In addition to the chains, there are also a lot of great upscale individual properties in the city, including the Peninsula right off Michigan Avenue where guests can enjoy treatments at the award-winning spa, tea in the sumptuous lobby, or out on the terrace, and Asian fine dining at Shanghai Terrace.

The lobby at Ian Schrager's trendy new Public Hotel.

There’s also an (unsurprisingly) over-the-top Trump Collection hotel here, a darling luxury boutique property called the Affinia near Navy Pier, where celebrity chef Marcus Samuelsson has a restaurant, and perhaps the most talked-about new hotel in town, Ian Schrager’s The Public, which opened in a 1926 building and embraces a casual ambiance, a minimalist-cool aesthetic, and one of the hottest restaurants in town, The Pump Room, with a menu by Jean-Georges Vongerichten.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.

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  • http://twitter.com/windycityf Windycityf

    A few more food suggestions, for pizza lovers try deep dish at Lou Malnatis or Gino’s. Also no trip to Chicago is complete without some Garretts Popcorn, try the Chicago Mix. Good news, you can now buy it at the the airport.
    2 other things White Sox play at Celluar Field, but we would accept Comiskey. And Marshall Field’s used to be a great place to shop but alas its been over taken by Macys and has lost it’s luster.

  • Selmer

    Don’t forget to visit The Second City comedy theater! A lot of big names and almost anyone who has been on Saturday Night Live got their start there…
    I’m actually planning a weekend in Chicago right now, but I probably won’t be able to go until June.

  • NTD

    I’m surprised you didn’t cover the newly branded Waldorf-Astoria Chicago in your Hilton section, the former (only 2 years-old) Elysian Hotel, which is ranked the #1 hotel in the United States on TripAdvisor, the #1 hotel in the United States by U.S. News, and is AAA 5 diamond. I’ve never even stayed there, but always been impressed by its newcomer status on the top of the best hotels list. And now that it’s a Waldorf (as of January 2012, I believe), it’s in the Hilton bracket!

  • NTD

    Looking back, oops- you mentioned it. But surely it should have gotten a bit more plugging!

  • Dbennett

    Marshall Field’s hasn’t existed for several years. It’s now Macy’s on State.

  • Wade Leishman

    Good Report, Chicago is a GREAT City for Kids… took my 4 year old twin girls there a couple years ago (from West Coast), and going back this summer… Children’s Museum, Navy Pier and everything else great for family’s!

  • guest

    Before the new Waldorf, the Conrad was probably the best Hilton in Chicago. There are sometimes great deals for suites as I got an Executive Suite for 43,000 points or so.

  • Lark

    I know you could not cover them all… But, as a Fairmont Platinum we are staying at the Fairmont Chicago. http://www.fairmont.com/Chicago/

    As you know with Fairmont, no points redemption options, but be did use one of our suite upgrades to upgrade to a Parkview Suite. For less than $300 / night, seems like a fabulous deal.

    We’ll be seeing the Cubs and the Sox during our stay – thanks for your other suggestions!

    Parkview Suite

    “What’s in a name? Not enough. We admit, “Parkview” doesn’t quite capture the grand view of Chicago’s legendary Millennium Park and Grant Park that is sure to capture your imagination from these large 700-square foot suites. But you’ll find the view inside our Parkview Suites is just as impressive. Feast your eyes on the fresh contemporary design that includes original Warwick Orme floral art, extra large closets and an impressively oversized marble bathroom. You’ll especially appreciate the separate walk-in shower, as its rainfall style shower washes your cares away. Plus, check out the lush sitting area, wet bar and a dining room for four. You’ll agree our Parkview Suites have a great view, wherever you look.

    Parkview Suites may be reserved with a second bedroom. Make a second reservervation for a Deluxe bedroom, king bed, and request to connect to the one-bedroom Parkview Suite.

    Bed Type: one King bed or two Double beds
    Size: 700 sq. ft.
    View: South toward Millennium and Grant Park, Buckingham Fountain, with partial Lake Michigan views ”

  • JL

    May is likely an awful time to go to Chicago this year as the NATO summit or whatever is in town and will be a huge distraction

  • Shorty

    Big props for your city series and for the Chicago highlights. I would like to also point out that I had a fantastic time and scored a great deal last summer at the Sofitel (watertower district) on Michigan Ave. Fantastic place with great service and a perfect location.

    The Art Institute is a must, and I have always enjoyed myself at the Shedd Aquarium.

  • Lzy402004

    Hey buddy, CONRAD Chicago is the best! I stayed there two times in the past months and it is 4 times better than Drake!

  • fabplacez

    Thank you for the great ideas. I greatly appreciate your effort in this article.

    http://www.fabplacez.com/weekend-escapes/weekend-in-chicago

  • Moly Mfg
  • Toni

    The Chicago Theater is also a great landmark to visit – it is beautiful inside and holds a lot of great history.

    And don’t miss Second City if you are a comedy lover.

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