Weekend Wanderings: Chicago

by Janis on May 12, 2011


Millennium Park, Chicago


12 Fun Things to Do in Chicago Regardless of the Weather 

Chicago’s central location makes it a perfect meeting place for a weekend with far-flung friends.

A high volume of flights into Chicago’s two passenger airports: O’Hare — one of the worlds’ busiest, and Midway — one of the most efficient, ensures multiple flight options.

Once you arrive, there’s fast, and easy-to-use public transportation downtown directly from both airports on the “L”. One way fare is only $2.25

We visited the “Windy City” in February. True to its reputation, the wind whipped off the lake, chilling the city even on a sunny day.  

Regardless of the weather, here are 12 fun things we discovered during our Chicago weekend wanderings.  

1. Stay at a hip hotel.  Conveniently located at 201 N. State in Chicago’s Theatre District, theWit  is just steps from State and Lake “L” stop for those arriving on the Orange line from Midway airport. Or, a two block walk from the Clark & Lake stop for those arriving from O’Hare on the Blue line.

Check in was a breeze with friendly and efficient staffers like Brittany. She got us in our rooms despite our early morning check-in. (Our friend flew in on a red-eye from Alaska.) Rooms at theWit aren’t large but have unique touches like designer sinks, colorful fabrics, and in-room literature with quirky copywriting.   

2. Where’s the beef?  We found it about 12 blocks from theWit at Al’s Beef, 28 East Jackson Boulevard.    “Junior, regular or giant?” was the greeting from the woman taking orders at the counter. As the first customers of the day and clearly not “in the know” at Al’s despite reading Yelp reviews, we asked for her recommendation.  “Beef and peppers with provolone,” and do you want it “dipped in gravy or on the side?” “And you can’t miss the fries.” We followed the advice and ordered with a side of “gravy”.  As promised, the fries were terrific, and the “gravy” is a garlicky au jus.   If you aren’t worried about clogged arteries, order the house special dipped in “Gravy”, to soften the crusty bread.

We intended make a comparison with Chicago other legendary beef joint, Mr. Beef on Orleans but ran out of time and eating capacity during this trip.

3. Sports and a cocktail?  Stomachs full of beef; we walked briskly to 134 S. Wabash home of Miller’s Pub  for a round of get-in-the-mood Bloody Marys. The five-part garnish could be another meal.  The bar at Millers attracts sports fans – both regulars and visitors in equal measure – who find it an ideal place to watch games while enjoying Greek and American comfort food.  

Lion at the Chicago Art Institute

A pair of lions flanks the Chicago Art Institute’s entrance.


4. European art. Now fueled, we were ready for culture.  The Art Institute of Chicago boasts an immense collection of European paintings. We enjoyed the Chagall’s America Window exhibit and the famous impressionist works by Seurat, Gauguin, Renoir, Monet and van Gogh, although the $18 admission price seemed kind of steep.

"The Bean"5. Outdoor park. Nearby, Millennium Park features outdoor art, including Cloud Gate artist Anish Kapoor’s polished sculpture inspired by liquid mercury. Nicknamed “The Bean,”  every visitor can’t resist checking out their distorted reflection.

6. Trendy roof-top bar.  Back at theWit, Chicago’s hipsters hang out at the indoor/outdoor rooftop bar, simply called  Roof.  During winter months it’s a terrific place to warm up by the fire, sip a specialty cocktail like our favorite Pears & Ginger and survey the Inner Loop. Late afternoons, the bar is busy but without the late night waiting line.  Hotel guests receive priority to get in Roof even if there’s a line extending around the corner.

7.  A pre-nap surprise. Tired from eating, walking, art viewing, and drinking, we returned to our rooms for a nap and found another lagniappe from theWit. A complimentary plate of house-made chocolates and lollipops was the perfect bite before snuggling into the comfy bed.


Juan is a fabulous bartender at Bin 36.

 8. Flights of wine and frommage. 

 90 minutes later, refreshed and ready for the evening we walked four blocks across the Chicago River to Bin 36 at 339 North Dearborn,   a restaurant, wine bar, cheese bar and wine retail store all combined into one.

We found three seats at the bar, where our favorite bartenders Juan and Johnny pour flight after flight of interesting wines –Bubbles to Sexy Reds to Ports. They recommend the best cheese flights to match each wine flight.  While a full dinner menu is available, we prefer the appetizers the hummus with warm pita bread and the spicy cheese balls with truffle oil and honey as we work our way through multiple wine and cheese flights.

9. Breakfast benefits. By booking theWit’s bed and breakfast option, we each received a $20 breakfast credit at State & Lake, the hotels first floor dining spot.  After a river of coffee, stacks of thick blueberry pancakes, a fluffy mushroom omelet, and a skillet cinnamon roll that served three, we were fueled for another day of exploration. What is it about the Chicago weather that fuels a hearty appetite?

10. Indoor entertainment. The freezing cold and rainy weather didn’t stop our fun.  We took a cab to Chicago’s Hyde Park neighborhood where the Museum of Science & Industry has acres of trains, planes, fast cars, body parts and science experiments to keep the young and old entertained for days. The coat check was also impressive, handling our wet coats, scarves and giant yellow theWit house umbrellas with ease.

11. Special Sunday night dinner. After an afternoon filled with science, we worked up an appetite, so we headed in a cab to the River North neighborhood. Tuscan-inspired Coco Pazzo  offers a warm atmosphere, delicious Italian food, and friendly yet impeccable service. A prior visit with locals taught us to order multiple courses to be served family style. We started with two appetizers: the wood fired pizza of the day and a fritto misto of lightly battered calamari, rock shrimp and vegetables.

Since the fresh pastas all sounded delicious, we ordered an appetizer portion of three recommended by our waiter, along with a Alto Adige Pinot Nero wine from the extensive Italian list.

Entrées we included the veal chops (carved into slices for our family-style sharing) and cod with scallops and roasted tomatoes.  For dessert, we shared a flourless chocolate cake, oozing with chocolate goodness and a perfect match for port.

12. Iconic shopping. Monday morning, provided a little time for shopping. While Chicago’s infamous Magnificent Mile is farther than a walk away, the former Marshall Fields, now Macy’s is just down the street, as is a large Nordstrom’s Rack. Perfect for quick shopping before catching the “L” to our flights.

Do you like Weekend Wanderings? Have you spent a weekend in Chicago?  What’s your favorite discovery? Be sure to share in comments!

Other Chicago posts to check out:  

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