17 Insider Chicago Tips

What does it take to be an amazing photographer? We know one proved recipe. Try being an amateur gardener, voracious reader, horrible golfer, and an occasional cyclist.  This is what out guest photographer Jordan does to keep taking perfect shots. You can also follow Jordan’s advice and attend an opera at the Lyric or a set at the Jazz Showcase. And, of course, one can’t go wrong with taking a stroll to explore one of the city’s many burgeoning and lively neighborhoods in Chicago for inspiration, admiration and romantic vibes. Find another 17 Insider Chicago Tips with us.

 

Here are 17 Insider tips for getting the most out of Chicago from Jordan

 

1. Favorite places in Chicago

 Garfield Park Conservatory:  This Jens Jensen designed masterpiece houses a wide array of plant species in the most glorious space. Just take one look at the Fern Room and you may be hooked. And, most importantly, it’s free.

Art Institute of Chicago: It may not be the largest museum around, but the Art Institute has a carefully curated collection that is full of masterpieces like Nighthawks, La Grande Jatte, and Chagall’s America Windows.

Oak Park’s Frank Lloyd Wright Historic District: Just nine miles west of downtown the works of Wright are everywhere in this small town. From Wright’s home and studio to the Unity Temple, one can get a sense as to why he still influences architecture today.

University of Chicago: With a campus that is perpetually expanding, there is always something new at Chicago (in local parlance). From Robbie House and the Oriental Institute, to new buildings and dorms popping up nearly every two years, the university is alive with activity.

Chicago Botanic Garden: North of the city, in Glencoe, this 385 acre oasis is free to the general public ­­– unless you are parking– and a nice place to stroll at any time of the day, any time of the year. Its 31 gardens and habitats will surely have something to grab your attention.

2. Three days in Chicago

If a friend had three days in Chicago, I would encourage them to bring a good pair of walking shoes.

Day 1:  Start at the Museum Campus (Shedd Aquarium, Field Museum, or Adler Planetarium) and/or the Art Institute and head to Grant and Millennium Parks to see gardens, public art and a wall of buildings whose styles span the century.

Day 2: Take an obligatory trip to the top of either the Sears Tower or the John Hancock. Make your way down to the Riverwalk and take an architectural tour on one of the many boats in operation.  End the day in River North with it many shops and restaurants.

Day 3:  Head out to Hyde Park, via the Metra Electric Line, and see the remnants of the Columbian Exposition of 1893 by way of  Jackson Park, the Museum of Science and Industry , and the University of Chicago. Then head over to 57^th St. to visit some of the city’s best bookstores and 53^rd St. to take in the local flair.

3. Chicago’s signature dishes

Oh, let me count the ways. According to Chicagoans we are famous for every dish, but pizza and hot dogs take the cake. When it comes to pizza, there is no right answer but Ricobenes on 26^th St. offers the traditional deep pizza along with thin crust and other Chicago staples. The Chicago dog is the same story, everyone has a favorite place, but Gene & Jude’s in River Grove is the best. It is a hike from downtown but worth the trip.

4. Favorite Chicago restaurant

Frontera Grill on Clark St. has been around for over 25 years and it is still one of the best restaurants in the city. Chef Rick Bayless’ cuisine offers a fresh and delicious take on tried and true Mexican dishes.

5. Best places to catch a sunrise or sunset

The best sunrise is at the end of Navy Pier when there are few people around.  Sunsets are brilliant in the West Loop when the skyline of glass and steel is ablaze.

6. Architecture photo shoots in Chicago

Along the Chicago River between Lake St. and Lake Shore Dr. you can take photos; on Wacker Dr., from the bridges, or from the riverwalk. Solidarity Drive by Solider Field offers and unobstructed view of the skyline and its major buildings. Lincoln Park from North or South Pond gives you endless chances to capture the interplay between nature and architecture.

7. Best way to spend a Saturday afternoon in Chicago

An afternoon in Old Town and Lincoln Park is a good place to start. One can traverse the narrow streets of Old Town and look at its turn of the century buildings. Then, head east to Lincoln Park Zoo or the Chicago History Museum; or head west to visit shops on North Ave. and Halsted St.

8. Ideal Sunday morning in Chicago

I usually like to walk around the Loop from Congress to Wacker Dr., and explore the streets when they are not teeming with people.

9. Most romantic places in Chicago

The Lurie Garden in Millennium Park, 31^st St. Harbor at sunrise or sunset, and the Osaka Garden in Jackson Park (currently under renovation).

10. Best breakfast or brunch in town

Though it may not be fancy, Valois in Hyde Park is my go to place for breakfast. This cafeteria is as much about people watching as it is about the food. Everyone from academics and politicians, to students and city workers frequent this spot.

11. Best coffee joint

Intelligentsia started out in Chicago and has since grown to have outlets nationally, but it still has the best coffee around. Be sure to visit the original shop on Broadway.

12. Favorite view of the city

Locals know Promontory Point in Hyde Park as an excellent spot to view the city. This peninsula juts out into the lake and has a rocky promenade where people can take a dip.

13. Most underrated sight in Chicago

Palmisano Park in Bridgeport: While it is only a few miles away from downtown – in a neighborhood known for politics above all else– it is truly an oasis. The site of a former quarry and landfill, the park now boast a wonderful hill (albeit man-made) and a fishing pond that is an unexpected sight in this dense community.

14. Best walking trail in Chicago

The Lakefront Trail: From the Ardmore Ave. to the South Shore Cultural Center this 18 mile path along Lake Michigan is the gateway to the city. Choose any mile marker and you are steps away from a new neighborhood with its sights, people, and traditions.

15. Best Chicago souvenirs

Chicagoans love their sports above all else like Russians love matryosha dolls and vodka, so take your pick of memorabilia; Hawks, Bears, Cubs, Bulls or Sox.

16. Chicago’s best kept secret

The Cook County Forest Preserves lie mostly outside the city but they are a place where one can go to walk, jog, bike, have a picnic, and even hike. With some 69,000 acres that surround city, the forest preserves are one of the area’s most precious natural resources.

17. What do you know about Chicago that most locals do not?

Chicago is home to the largest municipal harbor system in the country, with space for over 6,000 vessels at ten harbors.