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Crave Guide to Chicago

chicago-sign-blurby Steven Doyle

Today we begin what will be a series that checks in to various cities across the nation with a great history of tourism. Places to dine, great or boutique hotels across economic lines, and terrific sights that may be less traveled.

We begin our travel series with Chicago, often thought of for great dining and a history that is more than colorful. From storied tales of Al Capone, who still has a mark on the streets, to Oprah Winfrey, which is the ultimate Cinderella story, Chicago has a story for you to unfold.

The city’s waterfront location and nightlife has attracted residents and tourists alike. Over a third of the city population is concentrated in the lakefront neighborhoods from Rogers Park in the north to South Shore in the south. The city has many upscale dining establishments as well as many ethnic restaurant districts. These districts include the Mexican American neighborhoods, such as Pilsen along 18th street, and La Villita along 26th Street; the Puerto Rican enclave of Paseo Boricua in the Humboldt Park neighborhood; Greektown, along South Halsted Street, immediately west of down town; Little Italy, along Taylor Street; Chinatown in Armour Square; Polish Patches in West Town; Little Seoul in Albany Park around Lawrence Avenue; Little Vietnam near Broadway in Uptown; and the Desi area, along Devon Avenue in West Ridge.


The city is best seen from a bicycle, which are easily accessible. Chicago proudly ranks as the country’s best City for bicycling year after year because of its flat terrain, miles of bike trails, and interconnected neighborhoods, parks, and attractions. You can rent a bike from $3-$10 a day. Other suggested methods of transportation include Lyft and Uber, as well as the formidable train system. Parking and traffic usually excludes car rental, but that may be an option to consider. We used a combination of rideshares and the transit system during our recent visit with zero hiccups.

Also, you can check this article where you find information about how to ride with GPS mobile & Web compatible heatmap for better route planning

Where to Stay

The Blackstone

You will find all the top full-service luxury hotels including the Ritz-Carlton, Waldorf Astoria and the Four Seasons, but we found some fine boutique hotels recommended by locals. Check out Longman & Eagle which is a contemporary take on the traditional inn, with a great restaurant that is nose-to-tail with very reasonable prices and most dishes land under the $20 mark. Rooms begin at $95 a night.

We loved the Blackstone Hotel, another boutique housed in a 1910 beaux arts building across the street from Grant Park. The rooms are sultry and the suites are glamorous with  a full dining room, formal foyer, powder room and fireplace in some of the rooms. Room service is available, and the hotel features a Spanish restaurant. We found rooms for a little as $175.

The Peninsula Chicago offers luxury for the well traveled. The hotel features a rooftop spa, fabulous dining, and t’s centrally located in the heart of the city.  This is our upscale choice for Chicago.

Where to Dine

Located in Bridgeport neighborhood, Gio’s Deli supplied us with the finest example of a sandwich. At this tiny Italian-American deli we found a terrific example of an eggplant sub. Sloppy and well cheesed, the sauce was cause for consternation and 20 napkins. During our visit we sighted a group of Chicago’s finest and were told that is normal. Dine with the locals.  In addition to fine hot sandwiches you can explore a slew of Panini Freddi, wonderful pasta  Add to that dictionary, house-made ravioli and sauces bottled for home. Dare say you want your food spicy. The house-made Giardiniera is off the charts and made from fresh red peppers, jalapenos, carrots, celery and more.

Home-based in Dallas we were pleased to find Truluck’s downtown. This gave us reason to explore a vast assortment of seafood, including their signature stone crab. The restaurant features a special summer escape menu that includes a prix fixe meal for $55. We loved the lobster bisque,  which is on the escape menu, along with Caesar salad, Quahog clam chowder, beef medallions, scallops and more. choose three for a wonderful engagement. The steaks are marvelously charred for an indescribable grill flavor. Desserts cannot be missed, and your table should lay claim to the special trio of carrot cake, chocolate malt cake and a crème brulee. Heavenly in its brilliance.  Live music!

You may recognize Stephanie Izard from Top Chef and she has operated Girl and the Goat since 2010. The restaureant offers flavorful small plate served family style such as woodfired beets, soft shell crab, duck tongue, pork,  goat and beef sugo, crispy braised pork shank and a slew of fresh baked breaks.

Chinatown will draw you in, and you will want to taste the best pho this side of Ho Chi Minh City. Noodle Vietnamese Cuisine is the house favorite and it’s life changing. Located at 2336 S Wentworth.

Roanoke offers luxurious finishes, copper accents, and warm lighting were inspired by the fire of the rotisserie & brick oven at the display kitchen. Masculine lines are tailored to contrast with subtle historical references, some original to the 1913 building, for visual interest. Roanoke offers various seating options for every occasion,  and fine upscale dining.

Hutch was conceived based on two ideas; people want to be comfortable where they eat and what they eat and drink has to be craveable. Hutch represents just that, a warm and inviting place to truly enjoy yourself and food that is approachable, and most importantly delicious. This is a neighborhood restaurant where you can enjoy great cocktails, creative wine list and a menu for everyone. Bistro signature slow cooked baby back ribs, lobster nachos and grilled meatloaf.

Set in a former Masonic temple in Old Irving Park, Eris is a cider house and microbrewery pairs its signature beverages with New American comfort foods (many featuring cider or beer as an ingredient). The hip warehouse digs include communal tables, high tops and a long bar amid bare wood floors, vintage radiators and soaring ceilings with exposed beams and ductwork.

Obviously Chicago is steeped up in restaurants. These are our favorites now, and they skim economic lines. We also enjoyed Sushi-San, Fort Willow, Bellmore,and Rick Bayless’  Frontera Grill.

What About Hot Dogs and Pizza?

The primary difference between deep-dish pizza and most other forms of pizza is that, as the name suggests, the crust is very deep, creating a very thick pizza that resembles a pie more than a flatbread. Although the entire pizza is very thick, in traditional Chicago-style deep-dish pizzas, the crust itself is thin to medium in thickness. Deep-dish pizza is baked in a round, steel pan that is more similar to a cake or pie pan than a typical pizza pan. The pan is oiled in order to allow for easy removal as well as to create a fried effect on the outside of the crust.

Convention tells us that Uno’s as the first Chicago Deep Dish. Here we list a few pies that are traditionally thought of to be excellent pies, and we give our favorite as well. Everyone has their ultimate favorite.

Pizzeria Uno is where the original deep-dish style — a crispy short dough crust, topped with cheese first, then crushed tomatoes.

Rudy Malnati Sr. is one of the people credited with inventing deep dish at Pizzeria Uno, and his son Rudy Jr. launched this local chain. Unfortunately, Mama Malnati had already given the family pizza crust recipe to brother Lou for his own chain (see below), so she devised a new one for Rudy at Pizano Pizza.

Whether or not he invented it, Lou Manalti’s dad Rudy was present at the creation of what is probably the pizza that comes closest to what original deep dish tasted like. And this is a deep dish that extols the virtues of simplicity: buttery crust, a thick layer of cheese, bright canned tomatoes, and Italian sausage with a hint of wine.

Thick or thin, we enjoy Gulliver’s.

For those of you who are yet unaware, a Chicago style hot dog is comprised of the following: yellow mustard, white onions, so-bright-it’s-almost-neon green relish, a pickle (spears only, please), sport peppers, celery salt and tomatoes all atop a beef hot dog snuggled inside a poppy seed bun. Here are some favorites:

Gene and Judes: The location in River Grove – although known as Gene and Jude’s – originally had no name on the outside of the building and was called River Road Hot Dogs by many locals. There is no ketchup, no nonsense and no seats.

Fat Johnnies: Where else can you  find a double super dog and a tamale? The top  stands all carry tamales. Gotta love it.

Weiner’s Circle:  Best known for red hots, char-dogs and loving abuse

Gold Coast Hot Dogs: We  slammed a pair of these grilled dogs, dressed and delicious at Union Station minutes before loading up on  a train headed west. A perfect repast.

U.B. Dogs: One of the few we admire as much in the loop.

Don’t forget Italian Beefs such as Roma’s, Johnnie’s at 7500 W North Avenue, Mr Beefs, Bari and others – all greatness. Iconic and pure Chicago, composed of thin slices of seasoned roast beef, simmered and served au jus (known by locals as ‘gravy’) on a long Italian-style roll.

Where to Play

The Chicago Magic Lounge: The Chicago Magic Lounge is dedicated to re-introducing you to a style of magic created in the Windy City. Bar magic began in 1915 at a little place called Schulien’s. After that, over 15 Magic Bars opened up all over the city over the next 80 years. However, with the last one closing in 1999, the city has lost the true art of “Chicago-Style Magic”. Now, the magic is back. In the classic Chicago style.

Biking: Ride Through The City  Rent a DIVVY bike and see what the city offers. Biking is the best way to see the hidden treasures the city offer. Visit the many world-class parks and sites.  Use this guide to follow the trails.

Millennium Park: An instant hit since it was completed in 2004, this 24.5-acre park was named the top attraction in the Midwest in 2017. Among its many draws are Frank Gehry’s Pritzker Pavilion, which hosts free concerts and movie screenings in the summer; sculptor Anish Kapoor’s 110-ton Cloud Gate (a.k.a. “The Bean”); and Jaume Plensa’s Crown Fountain, with its ever-changing array of locals’ faces spewing water every five minutes in the summer months. The Lurie Garden wows with year-round flower displays and monthly garden walks.

Lincoln Park: Named for Illinois’s favorite son shortly after his assassination in 1865, Lincoln Park stretches six and a half miles along the lakeshore from Ohio Street Beach to Hollywood Beach. Inside the boundaries of the sprawling North Side park, visitors will also find attractions like the Lincoln Park Zoo 1000 animals, cost is free), the Lincoln Park Conservatory and the Lincoln Park Cultural Center. The park itself offers golf courses, baseball fields, a skate park and paths for walking, jogging or biking, as well as easy access to the nearby Lakefront Trail.

South Shore Cultural Center: Originally an early-20th-century country club, this gorgeous property was acquired by the Chicago Park District in 1975 and lovingly restored. These days, the main building hums with classes in the arts, culinary workshops, day camps and cultural programs; the grounds include a nature sanctuary, golf course, butterfly garden and plenty of beautifully maintained open spaces. Fans of The Blues Brothers may recognize the building as the exterior of the fictional Palace Hotel Ballroom, where Jake and Elwood performed a concert and eluded the police.

Chicago River: Chicago’s skyline is stunning from every angle, whether you’re on the sidewalk, in the back of a cab or cruising through the Loop on a train. But one of the coolest ways to take in all of the amazing architecture is through a boat tour on the river or Lake Michigan. Hop onboard and you’ll be treated to spectacular views of the most beautiful buildings in Chicago—you might even see some fireworks along the way. You can cruise the Chicago River, learning about the city’s vibrant history, or eat dinner and snap photos while gliding across Lake Michigan. Even if you’ve already visited the best Chicago attractions, you’ll appreciate seeing them from a new point of view on some of city’s best boat tours.

The Art Institute of Chicago: One of the city’s most well-known cultural institutions, which houses more than 300,000 artworks and an on-site restaurant, Terzo Piano (Italian-Mediterranean food). Acquaint yourself with classic paintings like Georges Seurat’s A Sunday on La Grande Jatte (as seen in Ferris Bueller’s Day Off) and Grant Wood’s American Gothic, or explore an expansive collection of contemporary works in the museum’s Modern Wing.

Wrigley Field: Built in 1914, Wrigley Field has been the home of North Side baseball team the Chicago Cubs for more than 100 years. Watch baseball at one of the oldest ballparks in America, sing along during the seventh-inning stretch and see one of the only manually operated scoreboards in existence, controlled by three members of the Cubs staff.

Green Mill: This Uptown cocktail lounge is a fixture of Chicago’s live jazz scene and has been slinging drinks since before Prohibition (Al Capone and other gangsters used to hang out at the Green Mill). Grab a seat early as it fills up and stays that way all night.

Second City: Bill Murray, Tina Fey, Stephen Colbert and Joan Rivers are just a few of the famous folks who honed their talents onstage at this theater devoted to sketch and improvised comedy. You’ll see some of the most talented rising comedic talents (and maybe a couple future Saturday Night Live cast members) on the Second City’s Mainstage. If you want to learn more about improv, stand-up or sketch writing, you can sign up for a class at the Training Center.

Navy Pier: Tourists flock to this stretch of attractions, which juts out into the waters of Lake Michigan. Navy Pier is home to a 200-foot Ferris wheel, the city’s only real IMAX screen, Chicago Children’s Museum, Chicago Shakespeare Theater and plentiful dining options. The sheer concentration of interesting things to do makes Navy Pier a great place for the whole family. See the city from a new perspective on the Ferris wheel, book a show at the Chicago Shakespeare Theater, board a boat tour or kick back with a margarita on a patio.

Art: On any given weekend night you will find a gallery opening soiree. Seek these out as they often have great art and cheap or free booze.

Where to Drink

Closing time for most pubs is 2am,  but a special license could grant you 4am or even a 5am closing time. Your favorite hard liquor selections may also be bought anywhere from 7am until 4am except Sunday where they make you wait until noon to create your own mimosa or bloody Mary.

Carol’s Pub: A honky-tonk Chicago style open until 5m on weekends with live music and adept drinking.

Murphy’s Bleachers: Open under one name or another, all with ‘bleachers’ in the title since the 1930’s, Murphy’s is  within homerun distance across the street from Wrigley Field.

Mordecai: Offers up terrific cocktails and food across from Wrigley. We might add that most of this area is filled with frat boys and sports bars, but this joint offers the largest selection of Pappy Van  Winkle in the nation.

Kingston Mines: There are few reminders left of Chicago’s legendary blues scene, with Kingston Mines in Lincoln Park perhaps the best. Open until at least 4 a.m. every night, stop by with a group of friends, park at the communal tables or stand by the stage, and listen to Chicago musical history while downing beers and Southern food.

Green Door Tavern: Billed as Chicago’s oldest tavern, the building was erected the year after the great Chicago fire (1872) and has been operating as Green Door Tavern since 1921—even during prohibition, as it’s one of the last surviving former speakeasies in town. Nowadays, patrons can feel the history and the local flavor in the main bar and restaurant. It also houses a new speakeasy, the Drifter, which is hidden behind a wall in the basement, offers a menu of some of the best cocktails in Chicago that’s printed onto a deck of Tarot cards, and has some of the most unique carnival-esque entertainment you’ll ever see.

The Aviary

Billy Goat Tavern: Walk downstairs from Michigan Avenue to Lower Wacker and into Chicago’s legendary Billy Goat Tavern, the namesake of the curse that made Cubs fans suffer for more than a century. A favorite of Chicago scribes and Saturday Night Live in the ‘70s, this spot endures as a friendly dive and burger joint to talk sports, politics and more.

The Aviary: Cocktails since unrealized from that amazing mind of Grant Achatz that are supremely whimsical, served with equally catching bites. If you are well equipped in the wallet check out his restaurants Alinea or Next restaurants which are unparalleled.

We left off plenty, some intentional or obvious, but there is so much to discover in Chicago and this merely a guide to start your holiday. . We hope you make the easy trip soon. We love Amtrak and Union Station should you have the time.

Thank you David Piper and Chicagoland weather girl Melissa Moore, our Chicago ambassadors. 

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