Visiting Chicago, IL - Jim Flynn's BestWeekends

Chicago, IL

Chicago, IL Overview

Anyone who has spent any time in Chicago quickly falls in love with this charming city. I lived there twice in my career and both my kids were born there, so it has a special place in my heart. Despite winters that can be quite brutal (ever been stuck in O’Hare in February?), Chicago has much to recommend it as a terrific weekend destination. You’ll find world class accommodations and dining, one of the best art museums in the world, a rich cultural tradition, the Cubs and Wrigley Field, Navy Pier, wonderfully diverse neighborhoods and in the Magnificent Mile, one of the best shopping stretches anywhere. Add a lakefront location (is there any other city that has urban beaches?), a gorgeous skyline, friendly Midwestern people, authentic Chicago Blues and that Saturday Night Live incubator, Second City and it will quickly go to the top of your “must see” lists.

When To Go

I love Chicago at any time of year, but the plains and the lake can make winters brutally cold and August very hot and humid. Spring is probably the best time to visit. The weather can be quite spectacular, it’s not too crowded and the already friendly people are even more so after a long, tough winter.

Getting There

Chicago is accessible by air from virtually anywhere in the country. Rail service is also available from both coasts. NY to Chicago by train is about a 28 hour trip. Taxi from O’Hare $40-$50. CTA: $2.25. The CTA from O’Hare is fast, efficient and inexpensive.

Getting Around

Taxis and Uber are abundant, public transportation is good and riding the “El” can even be fun.

Things To Do


No better place than along the lakefront which is easily accessible from most hotels. There’s 26 miles of unencumbered shoreline. Rent bikes at Bike Chicago which has locations at Navy Pier North Avenue Beach and Millennium Park.


Chicago Sailboat Charters, offers the opportunity to see the City from Lake Michigan in traditional sailboats ranging in size from 30-45 feet. Mid-day, sunset, fireworks and full moon cruises available. Pricing depends on boat and day of the week. Full crew to do all the work.

Another option is to sail aboard one of the “tall ships” . @$65 pp.

Ice Skating

The McCormick Tribune Ice Rink in Millennium Park is open from mid-November to med-March and is free and open to the public. Skate rental is $10.00. The ice rink is located on Michigan Avenue between Washington and Madison Streets. The Chicago Park District operates 10 rinks around the city.


Lots of good ones, but you won’t want to miss these, in order of importance. Art Institute, Field Museum of Natural History, Shedd Aquarium, Frank Lloyd Wright Home and Studio.


Here is a list of the most popular tours:
Gangsters & Ghosts Tour.
Big Bus Chicago Hop On Hop Off
Chicago Loop Secret Food Tour
Bikes, Bites and Brews
Chicago in a Day: Food, History and Architecture Combo Tour

Anyone who is remotely a baseball fan will want to take a tour of beautiful Wrigley Field, home of the beloved Chicago Cubs.


The art world in Chicago pretty much begins and ends with the world famous Art Institute which is both a museum and a school. The museum is home to over 300,000 works of art. Open every day at 10:30am. Admission $18.

Art Galleries

This is from Chicago Reader: 6018 North in Edgewater has a wealth of programming with thoughtful curation. Rogers Park’s PO Box Collective and Roman Susan project spaces and North Pole Exhibitions (a literal flagpole) will challenge in the best ways. Heaven in Wicker Park is still a hub for experimental work in a not-so-experimental neighborhood. 4th Ward Project Space in Hyde Park offers smart exhibitions, while the Comfort Station in Logan Square and the Breathing Room Space in New City/Back of the Yards give us a variety of art experiences with dedication to their communities.

Ready for more? Solid work can be found in East Village’s Roots & Culture, West Town’s Western Exhibitions and Volume, East Garfield Park’s Julius Caesar and Corbett vs. Dempsey, Bronzeville’s Blanc Gallery, and Pilsen’s ACRE ProjectsUri-Eichen, and Prospectus. I’d be remiss if I didn’t mention the Co-Prosperity Sphere in Bridgeport, the Stony Island Arts Bank in South Shore, and Bronzeville’s South Side Community Arts Center, continuously open since 1941 and a link to an art history in this city that is often forgotten.

Chicago Gallery News highlights all of the gallery events in the city.


Founded in 1954 the Lyric Opera is universally acclaimed and one of the most successful in the world. The season runs from October to March. The Chicago Symphony Orchestra was founded in 1891 and is hailed as one of the greatest orchestras in the world. Under the direction of Italian conductor Riccardo Muti, one of today’s most celebrated maestros, the symphony presents over 150 concerts a year.

Known for “Chicago Blues”, the city also offers virtually any other music genre in the many small clubs scattered throughout the City. See Chicago Music Guide and Vice.


Chicago has a vibrant theater scene and is often the last stop before a play lands on Broadway. The Red Orchid Theater Company is a Chi-town favorite.

Navy Pier

Originally a shipping and recreation facility and later a navy training base, Navy Pier today is a leading Chicago attraction welcoming 8 million visitors each year. Jutting out into Lake Michigan, the Pier offers a plethora of rides and attractions, music and theater productions, exhibits, tour and dining boats, restaurants, food courts, beer gardens, fireworks, shopping and more. It is open year round.


St. Patrick’s Day Paradejoins Boston, New York and Savannah as the best in the country.
Chicago Blues Festival. Late June. Grant Park.
Taste of Chicago-June. Grant Park. 70+ restaurants showcase their best products.
The Arlington Million-August. Arlington Park. Started in 1981. First race to offer a $1 million prize.
Chicago Jazz Festival-September. Millenium and Grant Parks.

Dont Miss

  • Outdoor concerts in Millennium Park
  • Navy Pier
  • The Art Institute
  • Shopping on the Magnificent Mile
  • Wrigley Field

The Best Of...

Local News

Here’s where you can find the local “scoop” before your Second City weekend. Newspapers: Chicago Tribune, Chicago Sun Times. Magazine: Chicago. Entertainment: Time Out Chicago.

Food & Drink


Of course, all of the hotels serve breakfast and all are good, but usually very expensive. $50 for breakfast for two is a bit much. For casual and light, I like Pierrot Gourmet at The Peninsula Hotel. Outdoor seating in good weather. Great bakery items. The Original Pancake House just off Michigan serves an inexpensive but good breakfast. Pancakes (get the apple ones), crepes, excellent chicken sausage. Lou Mitchell’s on West Jackson is famous for their breakfast…outdoor seating too. Ann Sather on W. Belmont serves breakfast with a Swedish twist. Swedish pancakes and to-die-for cinnamon buns. Fireplace warms it up in winter.

For something a little different, try the breakfast/brunch at Chicago Cut Steakhouse. Serves breakfast from 7am Mon-Fri and brunch from 10am on Saturday and Sunday. Wonderful riverside location with outdoor seating in nice weather. Fantastic menu.


All of the major hotels offer an excellent brunch, but I have never seen the likes of the one at The Lobby at the Peninsula Hotel. This would surely be your meal of the day because there is so much offered and at $75 you would certainly want to get your money’s worth, but it is something to behold. Take a look even if you don’t partake. North Pond is a great setting beside a pond in Lincoln Park, particularly in warm weather and they have a delicious brunch, although at $32, it is a little pricey. For something a little more moderately priced, but equally as delicious, I love Bistro Zinc on State Street. Great French bistro atmosphere. A la carte brunch. Super wine list.


So many choices, it really ends up being decided either by the type of food or the atmosphere you are looking for. For Mexican Frontera Grill is the place to go. Excellent guac and margarita’s. RL just of Michigan, (Ralph Lauren) is everything you would expect of RL. Beautifully decorated in wood paneled walls, area rugs, bookcases. Fireplace, small bar. Very happening. Noon arrival. No seats until 2pm. Cozy. Great Bloody. Outside tables in nice weather. Head to any Lou Malnati location for deep dish pizza. Love the LuxBar for New American and great people watching, particularly the outdoor tables. Le Bouchon and Bistrot Zinc are wonderful French bistros. Nothing like River Roast on a warm sunny day. East and West Coast oysters, roasted meats and fish. Killer Fried Chicken sandwich. Excellent lunch.


The Daily Meal voted the cheeseburger at Au Cheval, the best burger of 101 in the US. “The beauty of the burger served at Au Cheval lies in its simplicity: two patties (or three, if you order a “double”) of no-frills ground beef topped with Cheddar, Dijonnaise, and a few thin slices of pickles and served on a soft toasted bun from Chicago’s Z Baking. The patties are wonderfully crusty, and just about everything about this burger is perfect. The line to get into this place stretches literally around the block every day.”

Oyster Bar

Shaw’s Crab House has a great Happy Hour everyday beginning at 4pm. Drink specials and ½ price oysters. Pops for Champagne offers a selection of East Coast oysters and a wonderful champagne/Sparkling wine list.

Wine Bar

Wall Street Journal named Webster’s Wine Bar one of the top five wine bars in the US. Rootstock was opened by some former Webster employees and focuses on wine and beer of small production with a strong emphasis on organic and biodynamic farming practices. Features a local art exhibit. Eno is a warm, inviting spot with an excellent wine list and a fantastic cheese and chocolate menu. Cozy outdoor seating.

Picnic Fixins

It would be hard tot to find just about anything you would want for a picnic at Chicago French Market or Eataly.

Afternoon Delight

The Purple Pig, “Cheese, Swine and Wine” is a terrific place for a lite lunch, an afternoon snack or just to while away an afternoon. A collaboration of top chefs Scott Harris of Mia Francesca, Tony Mantuano of Spiaggia and Jimmy Bannos and Jimmy Bannos Jr.of Heaven on Seven was voted one of 10 “Best New Restaurants” by Bon Appetit. Some other favorites: Love LuxBar. Wonderful neighbor bar, open all day, with outdoor seating when the weather is nice and fireplaces for the cold. Excellent wine list. Have the Gold Coast Sliders. The Park Grill and The Plaza at Park Grill is a great afternoon spot in any season. In the winter you’ll overlook the McCormack Tribune Skating Rink and in the Spring and Summer wonderful al fresco dining on the plaza.


You certainly can’t beat the view from the 95th floor in the Hancock’s Signature Lounge or at The Terrace at Trump which has stunning views of the river and lake. Perfect place for the fireworks. Z Bar at The Peninsula is also a great warm weather venue. Pops for Champagne is loud and vibrant with a wonderful champagne menu, TV’s and small plates. Coq d’Or at The Drake is a local favorite. Le Bar at the Sofitel is very popular with terrific people watching, an excellent app menu, wine flights and great martinis. Maybe the best cocktail menu in town is at The Drawing Room on North Rush. For an excellent wine and cheese selection head to Webster’s Wine Bar. 

Amazing views of Millenium Park, Lake Michigan and the Art Institute make Cindy’s Rooftop a great choice for cocktails.

Irish Pub

The Galway Arms on North Clark has it all; atmosphere, the beers, the music, the food, soccer and a lot of blarney. Voted “best Irish bar” in Chicago Magazine.

Authentic German

Chicago is a city of nationalities….the Irish, Polish and German among the largest groups.The German population has enjoyed the The Berghoff on West Adams, since 1898. They got the first liquor license after Prohibition. Their Oktoberfest in Federal Plaza is legendary.


Steak is a religion in Chicago. All the best steakhouses serve prime beef with varying aging and cooking philosophies. Let’s assume all of the top steakhouses are very good, so who is the best? The chains, Morton’sCapital Grill and Ruth’s Chris are reliable and turn out a consistently good product. Chicago stalwart Gibson’s probably has the best vibe, people watching and amazing martinis. I love the décor at Chicago Chop House and they have a piano player and a Wine Spectator award winning wine list. You’ll enjoy a trip down memory lane at legendary Gene & Georgetti (and the best cottage fries).


After Dinner Fun

Symphony, opera, theater and pro sports offer lots of after dinner options. Click for tickets.You can enjoy drinks at any of the places we have listed under “Cocktails” above. Second City, the incubator for Saturday Night Live performers, will tickle your funny bone.  The Green Mill and Andy’s are legendary jazz venues and Kingston Mines Blues a great blues joint. Head to The Redhead or Howl at the Moon for piano bar fun. For something truly unique try Lincoln Karaoke where private rooms run $30 to $40 per hour and come equipped with couches, flat-screen TVs, a full bar, and a Korean menu featuring chicken wings and dumplings. Hideout is a very unconventional music venue that has been around forever. Small. intimate, very cool.


The Waldorf, The Peninsula and Trump all have amazing spa facilities, but they tend to be expensive. Although I guess if you are staying at these places, who cares. Nevertheless Heavenly Massage on N. State offers Manicures and pedicures for $30 and 55 minutes massages for $50.


These shops in Water Tower Place on Michigan Ave. can cover just about any memento from charms to Oprah merchandise to t-shirts, artwork and sports team gear. Local Charm, Oprah Store, Accent Chicago, Chicago Cubs Clubhouse. There are also many souvenir shops at Navy Pier.

Cool Shops

Lester Lampert, 90+ years of custom jewelry. Aroma Workshop, Over 100 oils can be made in perfumes, lotions, shampoos and other body care items. Fox’s has a great collections of designer duds at 40-70% off. Primative, One of the Midwest’s largest collection of artifacts, furniture, textiles, jewelry and clothing from around the world. P.O.S.H. Chicago, vintage and vintage inspired home and table accents.

Special Things

A Day at Wrigley

Even if you are not a baseball fan, Wrigley Field is one of the last great old ballparks and like Fenway in Boston, it won’t last forever. On none game days there’s a wonderful tour of the field, locker rooms and press box.

A Sunrise on the Lake

Grab a cup of coffee, early in the morning and head over to Lake Michigan for a wonderful stroll as the sun rises over the water. Terrific way to start the day.

Sunset Over the City

You can enjoy the glorious sunsets over the city at a luxurious dinner at Everest from the 40th floor of an office building or just for drinks at the Signature Lounge on the 95th floor of the Hancock Building.

Where To Stay

Peninsula Hotel

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OVERVIEW of the Peninsula Hotel

Since 1928 Peninsula Hong Kong has set the world standard for exceptional service, style and comfort. In 2001 Peninsula Chicago opened and quickly reached the pinnacle of American hotels. It is consistently rated one of the top three or four hotels in the country. View Property Details

Sofitel Hotel

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OVERVIEW of Sofitel Hotel

Sofitel Hotels are a favorite of ours and are recommended in our New York, Washington, DC and LA profiles. As I have said before you get a 4 star experience at a 3 star price. Their weekend rates are amazingly reasonable given the style and ambiance you enjoy. View Property Details

Trump International Hotel

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OVERVIEW of Trump International Hotel

Say what you want about Donald Trump, the man knows how to do a hotel right and the Chicago incarnation is no exception. Located in the Loop beside the Chicago River, the soaring 92 story Trump is a bold design against…

View Property Details

Waldorf Astoria

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OVERVIEW of Waldorf Astoria

It is not often that a new hotel enters a major city and takes it by storm... almost immediately. This is particularly true in Chicago which boasts some of the best hotels in the country. But that is what happened with the View Property Details

Where To Eat

Gibson’s Bar and Steakhouse

There may be better steaks in town, but it is tough to beat the vibe at Gibson's in the heart of the Gold Coast. A favorite of locals for years, it is also a "must stop" for visiting celebrities and sports stars. Seldom will you dine here without seeing someone famous. You just can't help…

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Le Bouchon

I have a soft spot for French bistros and they don't come more authentic than Le Bouchon, a low-key, relaxed, bistro, which from the outside, looks like a traditional Irish/European pub. Inside, the tiny restaurant is intimate and classically decorated with warm booths, colors of beige and red, wicker baskets, floral arrangements and historical French…

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Les Nomades

If pedigree means anything to the success of a restaurant, then it explains Les Nomades perch atop the list of Chicago restaurants. Owner Mary Beth Liccioni and her husband Chef Roland spent a portion of their career working with acclaimed chef Jean Banchet at Le Francais in Wheeling and later bought the restaurant from Banchet.…

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North Pond

North Pond offers one of the most delightful settings in the City, nestled in Lincoln Park overlooking a Pond. When the weather is nice, dining outside is a treat and even in the winter, inside beside the fireplace it's warm and cozy. The interior is decorated in light woods, with hardwood floors, high ceilings and…

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The setting for Spiaggia couldn't be more dramatic. Tables in the two tiered dining room face huge windows looking out on Michigan Avenue and the lake. The dark, intimate room with flickering candles and fresh flowers is the perfect place for a special occasion. Spiaggia has been a Chicago institution for nearly 30 years. It…

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Webster’s Wine Bar

If you are a wine lover and are looking to enjoy some wonderful wines and a casual meal or snack, Webster's Wine Bar in Lincoln Park is the perfect place. It's Chicago's oldest wine bar, some 30 years old and I think, still the best. With tasting events, wine trips, wine dinners, live music and…

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