For spring and summer few cities offer more choices for entertainment.

Still known as “Chi-Town” by many, as well as “The Third Coast” or “Second City” by others, Chicago is as multicultural as it gets.

On a short stroll, you can actually sample the music, food and culture of almost any nationality – especially in the Downtown area, which is why most foreigners and first time US visitors come to love the city after just one visit.

Park & Trek

Locals tend to leave their car in a safe paid lot or a free parking spot on the edge of the CBD from where you can hoof or cycle along the parks and miles-long pathways bordering Lake Michigan. It’s also a daily commute route for many people who choose to bike rather than drive to work.

Bicycle rentals are available through companies like Chicago Bike and Roll, which has bike rental spots all around the downtown area. The choices include hourly or daily rentals of single-seat, tandem, group-pedal quad-cycles and any other forms of pedal powered transport. Rates vary from US$8 per hour up to US$69 a day. If you want to “take it up a notch,” and avoid pedalling you can join a fun, motorized two-wheel “Segway” tour with a professional guide. A 2.5-hour tour of the lakefront during daytime or at sunset costs around US$69, or US$59 for kids.

Trails exist all along the lake from the far southern tip in Indiana all the way north to Wisconsin, so serious bikers can actually take days for their jaunts. Tours, self-made or paid, need not be linear at all, as there are many areas to explore off the main routes. Caution, of course, is advised when biking as the lakefront can get quite crowded, especially during warm weather periods, with inline skaters and some bicyclists hitting high speeds.

Local Favourites

One of my favorite bike trips loops around the entire museum campus south of downtown. I branch out to Northerly Island and Adler Planetarium, both with striking skyline views, day or night. I favor cleaving along the lake where it borders Monroe Harbor, and if the waves are not too high, heading along the angled stretch just between Lake Shore Drive and the lake.

You might prefer to divert inland and walk amid the many unique gardens of Grant Park or the Lurie Garden prairie plantings, just east of Millennium Park. Art is wondrously mixed with flora and intriguing water displays. The area abuts various cultural institutions and has been lovingly tended for years.

Consider Buckingham Fountain as your rest stop on such a trip. It boasts stunning gardens and spray water jets seemingly as high as some of the nearby skyscrapers. Millennium Park also holds amazing summer concerts, with world music and classical performances highlighted on the stage surrounded by many famous buildings, including Prudential Tower and others along the “Magnificent Mile” of Michigan Avenue, which stretches from there northwards.

Grant Park hosts “Taste of Chicago” with food on offer from the city’s myriad eateries, as well as Jazz, Gospel, Blues and other super music festivals. Also found there are constantly changing outdoor art exhibits, as well as dance performances, small and large concerts and crafts fairs.

Eat & Keep Moving

You can dine at the park’s own restaurants, of which there are quite a few, and enjoy top quality mid- to high-priced meals. Vendors sell from approved stands throughout the park and the street is lined with restaurants from every nation. I often sit in the Art Institute’s shaded areas to watch the world pass, many people straining to see the soaring structures above. The Institute sells take-away food and also has restaurants inside.

A world of delicious dining is close at hand when you’re in “the Loop”. Pierogi Heaven serves up amazing Polish fare at great prices, BenjYehuda offers cheap Mediterranean and Middle Eastern foods, Osaka Express Inc has quick-serve Sushi and other Japanese eats, Protein Bar’s quinoa-based dishes, parm bowls, burritos are great, Artist’s Cafe excels in artisan sandwiches, wraps, salads and pastries, while Miller’s Pub has quality pub fare, pizzas, and nice booths for chowing down.

To save legwork on a full stomach you can always use other modes of transportation in Chicago. The city’s transport network is great and includes a section of the metropolitan area’s part-subway rail link, “The E.L” (for “elevated” and the “L-shape” it takes through the urban landscape). You’ll hear the trains or see their elevated tracks and stations every few blocks around downtown – there are ramps down to subway sections, as well.

Buy Chicago Transit Authority (CTA) multi-trip “Ventra” passes at machines in stations, but note that CTA lines are not related to Metra trains. The latter have different routes, slightly more costly tickets and cushier seats, and have fast lines to many far-flung suburbs and towns not served by CTA. Taxis are also plentiful around downtown, though pricey by comparison, of course.

Fun & Learning

For supreme but educational entertainment, take a Chicago River boat tour through the city, and another one along the lakefront. The latter is amazing when done in the Spring or early summer, as you’ll not get a better view of the city’s skyline unless you know a private boat captain.

I learned more about Chicago history on one boat trip and walking tour than I did by reading guide books. The Chicago Architecture Foundation offers numerous cruises, on Chicago’s First Lady yachts. They start dockside at the crossing of Michigan Avenue at Lower Wacker Drive. The 90-minute river cruises are by far the best.

Trained docents explain the history of each famous structure, which is usually seen only from the street. The Chicago Opera House, Merchandise Mart, the Wrigley Building and up to 50 well-known buildings of the city have striking stories that offer peeks into the city’s wild and wonderful past. Tours on the Lake and along the shoreline are therefore a refreshing adventure in history.

The yachts hold up to 200 passengers (I prefer the smaller ones: more cozy), have full-service bars and well-appointed marble and granite washrooms – so these are not old rusty tubs by any means. Enjoy outdoor upper decks or air-conditioned lower-deck indoor cabins. Spend more money to get a romantic cruise for two, or charter mid-sized vessels for private parties with great, catered cuisine and private bands.

If you’re planning to be in the Chicago area on July 4th, reserve a ticket ahead of time to enjoy the lakeside Independence Day fireworks accompanied by radio-matched music. I still recall these wonderful experiences over a decade later, and you’ll remember them for a long time too.

Walking tours, train and bus tours abound in Chicago, with a range of different tours through the downtown and broader metro areas. Some bus lines also offer hop-on-hop-off trips to various Chicago attractions.


In Chicago be sure to visit the following world-famous treasures – all reachable via public transport, walking, cycling or on a tour of some kind.

  • Chicago Art Institute – a goldmine of ancient and modern art, with special exhibitions on display,including photography (www.artic.edu).
  • Shedd Aquarium – set directly on the Lake, it offers prime views out and an amazing variety of sea life to watch cavorting inside (www.sheddaquarium.org).
  • Field Museum of Natural History – is full of interesting objects: life-size (man-made) dinosaurs, numerous plants, animals, masks (www.fieldmuseum.org).
  • Navy Pier has many draws, like the Chicago Children’s Museum, a cool games section, an Imax theatre, unreal gardens, and more (www.navypier.com).
  • Lincoln Park Zoo has a petting section for children, an enchanting aviary, and peaceful gardens nearby. (www.lpzoo.org)
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Jim Grubman
Jim Grubman has lived more lives than the average cat, though he's hoping his two Flame-Point Himalayans beat him. He has written and edited many things, including cookbooks (he's a qualified chef), and he has even saved lives as a dialysis technician among a long list of medical and other jobs. For fun, he travels, writes about it, and sails as close to the Southern Seas as a sane man dare try.