10 Offbeat Things To Do In Chicago

If you’ve never been to Chicago, or you’ve only visited during the winter, which tends to last roughly from early fall through late spring, you have to see the place in the summer. As soon as the weather gets warm, the city’s residents flock to the lakefront and the place buzzes with live music, street festivals and places to dine al fresco.

The typical tourist itinerary includes stops at the Art Institute, Navy Pier, a boat ride on the lake or the river, Wrigley Field, the Magnificent Mile, and the Willis (Sears) Tower, among other places. If you’ve already been to these places, or you’d rather dig deeper and go further off the beaten track, here are ten more under the radar things to do in America’s Second City.

10. Jam Sessions at the Old Town School of Folk Music
Chicago is loaded with great places to hear live music but I have a soft spot for the city’s free jam sessions and this place is one of my favorites. They have two locations – one in Lincoln Park and one in Lincoln Square – that host live shows and classes. The Lincoln Square location has jams on Wednesdays from 12 – 2 p.m. and Thursdays from 7 – 10:30 p.m. and the Lincoln Park location hosts jams on Saturdays from 12 – 1 p.m. You never know who’s going to show up but it’s a great place to listen to live music and to meet locals. (Or if Bluegrass is your thing, head to the Montrose Saloon on the second Wednesday of each month for their open jam.)

9. St. John Cantius Church

Chicago has plenty of atmospheric old churches but I’m partial to this baroque beauty in the city’s hip Bucktown neighborhood. The church was built around the turn of the 20th Century by Polish immigrants and it has some incredibly beautiful stained glass. And if you love to visit historic churches, get on 90/94 West a couple miles north to check out the Our Lady of Sorrows Basilica, another turn of the century beauty which still hosts masses in Polish on Sunday mornings.

8. National Museum of Mexican Art

I dig this museum, located in the city’s Pilsen neighborhood, because the works of art tend to be colorful and accessible rather than abstract. It’s free and they have a terrific gift shop that is filled with great gifts that are handmade in Mexico, including loads of Day of the Dead themed items.

7. Bookman’s Corner

My wife refuses to step foot in this fire hazard of a bookshop but I’m addicted to the place. John Chandler, who has been selling used books “rare, medium and well done” at this Lakeview shop since 1984, is a character. It’s worth a trip to this place just to listen to him shoot the breeze with some of his regulars who stop in to buy and sell books on Saturdays. There are books everywhere, so watch where you step. I’ve had books come crashing down on my head here and if you pull something out of a big stack, the whole pile might come crashing down on you like an avalanche. But I always leave with something unexpected and the prices are unbeatable. Just don’t ask John if he has a specific book because trust me, he’s not sure.

6. Traditional Irish Music Sessions

I spent a summer in Galway in college and have been hooked on traditional Irish music ever since. Chicago is a great place to take in a free Sunday “session” where you’ll hear some great music and meet plenty of colorful Guinness quaffing locals as well as visitors and expats from Ireland and Scotland. My favorite Sunday sessions are at Tommy Nevin’s Pub in Evanston, a great little town just north of the city (3-6 p.m.), the Abbey Pub (4 p.m.), the Grafton (5-8 p.m.) and the Galway Arms (8 p.m.) (If you prefer classical music, try the free weekend concerts at the Julius Meinl Cafe on Southport.)

5. Neighborhood Beaches

On a sunny day, you can’t go wrong with any of Chicago’s beaches, but the Ohio Street and North Avenue beaches can be ridiculously crowded on warm summer weekends, so head further north along the bike path to carve out a little more space in the sand. If you’re a dog owner or a dog lover, you’ve got to check out the Montrose Dog Beach; if you’re looking for a gay beach, Kathy Osterman Beach is a good call; and if you want a beach with plenty of sports and recreation opportunities, check out Foster Avenue Beach. If you just want to photograph the city skyline, go south of the city to Promontory Point in Hyde Park. I like to cap off a summer day at the beach with dinner or drinks on the rooftop deck at Pegasus in Greektown, which has great food and views of the skyline.

4. The Money Museum at the Federal Reserve Bank

Inside Chicago’s Federal Reserve Bank you’ll find this interesting little museum, where you can see and have your picture taken with old and rare coins and bills, including $5,000 and $10,000 bills. They have a free 45 minute guided tour at 1 p.m., Monday-Friday and on your way out you can pick up a bag of “Fed Shreds,” which is $300 worth of shredded, uncirculated money. (Good luck trying to piece your bag of money back together again.)

3. A Taste of Arabia in Albany Park

Take the Brown Line train up to Kedzie to get a flavor of this fascinating neighborhood, which has some of the best Middle Eastern restaurants in the city. I love walking on Kedzie between Montrose and Lawrence to check out the Arab shops, bakeries and restaurants. My favorite places to eat on this strip are Al Khyam (Lebanese),Noon O Kabab (Persian), and Salam (hole-in-the-wall pan Arab). For after dinner sweets try Jaafer Sweets.

2. Richard H. Dreihaus Museum

A visit to Chicago’s old Nickerson Mansion will transport you back to the Gilded Age. I took a tour of the place with my family in March and was floored by the ornate stained glass, the Moorish inspired décor and all of the amazing period furniture. There is no better place to get a feel for how the city’s elite lived at the turn of the 20th Century.

1. Devon Avenue

You don’t have to leave the Midwest to travel to the Indian subcontinent. Just make your way to Devon Avenue near Western and you’ll be in a place where saris, turbans, and shalwar kameezes are the order of the day. This is often referred to as an Indian neighborhood but it’s both Indian and Pakistani. You’ll find Gandhi Electronics right across the street from an Islamic Finance Bank and both communities- Hindu and Muslim- seem to coexist nicely here.

Most visitors come here to eat. My favorite restaurants are Annapurna – a hole-in-the-wall spot which has a $3.49 lunch special – Hema’s Kitchen, which has a killer vindaloo, and Urban India, which has the best garlic naan in the city. While in this hood, I also like to walk down to the Georgian Bakery, which has great bread and Georgian specialties like khachapuri (a cheese pastry) and khin-kali (meat dumplings).

I also like to pop into the sari shops, the Indian video stores, the House of 220 Volt Appliances, which has suitcases big enough to store baby elephants, and the food shops, were you’ll find some treats that might make Andrew Zimmern blush. On Michigan Avenue, you’ll be tripping over other tourists, but on Devon Avenue, you’ll be tripping over 50 pound sacks of basmati rice and flowing saris. The choice is yours.

[Photo credits: Dave Seminara, Viewminder, Clint McMahon, and Swanksalot on Flickr]