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A Local’s Guide to Chicago | Don't Ever Look Back

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A Local’s Guide to Chicago

A Local’s Guide to Chicago

About the Author: Katie Aune is a thirty-something recovering attorney who has lived in Chicago for nearly 10 years.  She has a passion for travel and sports, combining the two whenever possible.  With a full-time job in nonprofit fundraising, she takes full advantage of her vacation time to travel internationally at least once each year, but harbors hopes of one day embarking on a long-term trip through Russia and the former Soviet Union.  Follow Katie’s adventures at www.katiegoingglobal.com or on Twitter at @kgoingglobal.

Like many large cities, Chicago has its share of typical tourist attractions – great museums, Navy Pier and the Willis (formerly known as Sears) Tower.  But having lived here for nearly ten years, I can assure you, the city has so much more to offer!

Chicago in the Summer

Lollapalooza and the Chicago Skyline

Lollapalooza and the Chicago Skyline

I recommend visiting Chicago between June and early September when you can stroll through Millennium Park, pick up a game of volleyball at North Avenue Beach, or ride a bike along the many miles of our lakefront bike paths. Sports-lovers can catch one of the city’s two baseball teams in action – the Cubs at historic Wrigley Field or the White Sox at the more modern and spectator friendly U.S. Cellular Field. Or, you can just spend your time the way many Chicagoans do – hanging out in one of our many beer gardens, sidewalk cafes and rooftop bars.

Chicago’s street fairs and music festivals are the highlights of the summer.   Some of my favorite street fests include German May Fest (late May/early June), Old Town Art Fair & Wells Street Art Festival (mid-June), Taste of Randolph Street (mid-June), Old St. Pat’s World’s Largest Block Party (mid-July), Retro on Roscoe (mid-August) and German-American Festival (early September).  With the exception of Old St. Pat’s, most ask for a $5-$10 donation for entrance and offer food and beer for sale, a variety of vendors and multiple stages of live music.

Chicago’s Pride Parade typically attracts close to 1 million spectators and completely takes over the Boystown neighborhood the last Sunday in June.  I usually enjoy brunch (with bottomless mimosas!) at Duffy’s Tavern near the end of the route before going outside to catch the parade. Music-lovers may want to consider planning their visit around Blues Fest (June 10-12, 2011), Pitchfork Music Festival (mid-July), Lollapalooza (August 5-7), Jazz Fest (September 2-4) or Country Music Fest (October 1-2).

Visit www.metromix.com in late spring for a full guide to the summer fairs and festivals.

Enjoying Retro on Roscoe

Enjoying Retro on Roscoe

Chicago in the Winter

If you can’t make it to Chicago in the summer months, the next best thing is to plan a visit between Thanksgiving and New Year’s.  You can participate in Christmas carol sing-a-longs at “the Bean” in Millennium Park, enjoy a glass of mulled wine and a hot pretzel at the Christkindlmarket in Daley Plaza or take in the Thanksgiving Day Parade on State Street. Or grab a pair of skates and hit one of the ice rinks outside Wrigley Field or at Millennium Park – or even inside on the 94th floor of the John Hancock Building!

If you enjoy day drinking and bar hopping, you definitely don’t want to miss the Twelve Bars of Christmas (TBOX) bar crawl in mid-December.  Going fifteen years strong and attracting nearly 10,000 people in 2010, it features opening and closing ceremonies, people toting boxes of cereal to do “cereal shots”, drink specials at 37 Wrigleyville bars and, best of all, thousands of people dressed up in ridiculous holiday-themed costumes (think elves, Christmas trees and slutty Santa’s helpers).  But really, when the weather turns cold, many Chicagoans just head inside and do what we do best: drink and watch sports, whether it’s cheering on our favorite college football team or the local pro teams – the Bears, Bulls and Blackhawks.

View of Lake Michigan from the Willis Tower

View of Lake Michigan from the Willis Tower

Getting Around

One of the great things about Chicago is its public transportation system, the CTA.  One card works for both buses and trains and the system is extraordinarily easy to figure out, with maps at every train station and most bus stops.  The CTA will take you from either Midway or O’Hare airports to downtown in 45 minutes or less – no need to spend $30 on a taxi!  The Red Line is the main artery of the city, running north to south 24/7, and the line you’re most likely to ride to get from place to place.  Visitors can buy a Visitor Pass, which is $14 for 3 days or $23 for 7 days.  Considering a single ride paying cash is $2.25, this can be a great deal.  You can find train and bus schedules and a trip planner online at www.transitchicago.com.  If you’re taking the bus, the CTA also offers an online bus tracker to check arrival times. A train tracker is supposed to be launched any day now.


When most people think of Chicago cuisine, they likely think of what the city is most famous for – deep-dish pizza and the Chicago-style hot dog. Now, while I would never discourage anyone from sampling either, Chicago has a lot more to offer.  One of my favorite places is Café BaBaReeba – a festive Spanish tapas place in the Lincoln Park neighborhood.  It has a fun atmosphere, great food and excellent sangria, all while being reasonably priced and easily accessible by the Brown Line from downtown (Armitage stop).   I also love the city’s BYOB restaurants.  Found almost everywhere, these can be a great bargain, allowing you to save money on alcohol by bringing your own beer or bottle of wine (a corkage fee will usually apply).  I personally love Los Nopales, a Mexican restaurant in the Lincoln Square neighborhood (take the Brown Line to Western), as well as Tango Sur in Lakeview (Brown Line to Southport), an Argentinian steakhouse that will not leave you hungry!

What I love about Chicago is that you can literally eat your way around the world while visiting many of our ethnic neighborhoods at the same time – and all by riding the CTA.  Take the Red Line south to Chinatown for authentic Chinese or dim sum – my personal favorites are Lao Sze Chuan and Three Happiness (for dim sum).  For Mexican, head west on the Pink Line to the Pilsen neighborhood – there are some great options along 18th Street, but I recommend Nuevo Leon. Much further north, but definitely worth the effort, head up to Devon Avenue for incredible Indian food.  Tiffin is my choice here, but you really can’t go wrong with any of the places along Devon between Western and California.

Of course, if you do want to try out Chicago’s famous deep-dish pizza, Giordano’s and Pizzeria Uno are two of the best.   And Hot Doug’s is the only way to go for a Chicago-style hot dog.  Less than half a mile from Hot Doug’s you can also find the burger capital of Chicago (and maybe the world?!) – Kuma’s Corner.  Be prepared to wait, but I guarantee that you will not be disappointed!  For other restaurant ideas and reviews, try Yelp Chicago or Check Please.


Blues at Kingston Mines

Blues at Kingston Mines

Chicago’s nightlife has something for everyone.  Many visitors never stray much beyond the River North area, which isn’t necessary if you love club-hopping and celebrity-spotting.  $20 cover is not uncommon and be dressed to impress (guys, no tennis shoes or sleeveless shirts).  Some of the hot spots include the Underground, Cuvee, Enclave and the Roof at the Wit Hotel.  Clubs are constantly coming and going, though, so check www.redeyechicago.com or www.metromix.com for the latest.

For a more laidback scene, head further west or north.  You’ll find an array of sports bars and Irish pubs along Lincoln Avenue in the Lincoln Park neighborhood or Clark Street in Wrigleyville (take the Red Line north from downtown to Fullerton or Addison). I personally like Casey Moran’s, Vines and the Irish Oak.  The Wicker Park and Bucktown neighborhoods also have a lot of options – head to Division Avenue near Damen or the intersection of North, Milwaukee and Damen Avenues (accessible by the Blue Line from downtown).

If you’re looking for live music, there is no shortage of venues to explore – try the Double Door, Schuba’s Tavern, Reggie’s, Lincoln Hall or the Metro, all of which showcase both local and national acts.  For a great Chicago blues experience, check out Kingston Mines in Lincoln Park or Buddy Guy’s Legends in the South Loop and for jazz, try the Green Mill in Uptown or Andy’s Jazz Club downtown.


Finally, where to stay?  Most hotels in the downtown area will run you at least $200 a night, likely more.  For cheaper and cuter alternative, try a bed & breakfast.  I didn’t even know these existed in Chicago until an Australian friend visited and stayed at one – a basement apartment equipped with a full kitchen and laundry for only $125 a night!  Try www.chicago-bed-breakfast.com for a few options.  If you’re really on a budget, Hostelling International has a 500-bed hostel in the heart of downtown with beds as low as $29 a night.  The hostel also provides guided tours of the city and discounts on museums and other attractions.

I could probably go on forever about all the great things to see and do in Chicago (thank goodness for word limits, right?), but hopefully this gives you a good taste of what you can expect when you visit.  I hope to see you here soon!

Flickr Photo: Nimesh M


  1. Posted January 17, 2011 at 1:53 am | Permalink

    Thanks for the insider scoop!! Next time I am planning a trip to Chicago, I will definitely refer back to this post!

    On two separate trips, my fiancée went to The Clark St. Dog for the most amazing Cheese-steaks ever!! We found them on a fluke the first time when we were waiting to go see The Blue Man Group. The second time, we were just passing through Chicago, and made a special trip to eat there. It was just as good the 2nd time!! Just thought I would put that out there as another must when visiting your beautiful city!!

  2. Posted January 17, 2011 at 3:08 pm | Permalink

    Thanks Sarah! I haven’t been to Clark St Dog, but I’ve heard it’s good as well. Hope you’re able to make it Chicago again soon!
    Katie recently posted..A Guide to Completing Your Career Grand Slam as a spectator

  3. Posted January 17, 2011 at 4:14 pm | Permalink

    I LOVE CHICAGO! I’d move there if it weren’t so cold! But my best friend lives there so I’ve visited many many times. You forgot to include BOYS TOWN on your list! No seriously – the most wild nights of my life.

    Great list! I’m dieing to go to a Cubs game! It’s such a beautiful city. I’d love to spend a summer there. 🙂
    Lauren Rains @ TheMa recently posted..An Anti Lazy POS Lifestyle Design Travel Story

  4. Posted January 18, 2011 at 4:54 am | Permalink

    Hey Katie! Great post. We love Chicago too! Have you checked out http://upchicago.com? It’s a new alternative Chicago city guide we think you’d love!
    UPchicago.com recently posted..My Sweet Home Chicago- Gene Wagendorf III

  5. Posted January 18, 2011 at 9:41 am | Permalink

    Chicago has been on my list of places to return to as an adult that I have been to as a child and since I have a friend in school there at the moment, I just booked a flight for the first week in April. This post came at a perfect time!! I am saving it and checking out the links:-).

    I am also there during Baconfest, which I think you wrote about on your blog(?) and I am seriously debating weather to attend. It looks AWESOME!
    Rebecca recently posted..San Francisco – Bars- The View- Thirsy Bear and Public House

  6. Posted January 18, 2011 at 1:02 pm | Permalink

    Great detailed guide, seems like a real fun place to visit in summertime!

  7. Posted January 18, 2011 at 1:14 pm | Permalink

    Excellent post!! I would definitely recommend Chicago in the summer though – Jess, who is from Chicago, took me to her hometown in December for the first time, and I almost froze my toes off 😉 In the summer you can enjoy the gorgeous beaches, ride bikes along Lakeshore Drive, hang out in Millenium Park… and visit The Taste Of Chicago – my favorite Chicago event! Jess loves Cafe BaBaReeba too, and we’ll definitely check out Los Nopales next time we’re in town.
    Globetrottergirls recently posted..Polaroid of the week- Climbing for coconuts on Little Corn Island

  8. Posted January 18, 2011 at 3:24 pm | Permalink

    I can’t wait to get back there 🙂 I’ll be in Chicago at the beginning of June for a few days before heading south to Peoria. I’m gonna eat me some Giordano’s and a damn good hot dog! Can’t wait!
    Brooke, WhyGo Austra recently posted..Australia Travel News 01-17-2011

  9. Posted January 20, 2011 at 5:44 am | Permalink

    I was thinking of planning a trip to Chicago since the airfare is so cheap from Denver. These are great tips I will have to print out and follow if I go. Thanks!
    Suzy recently posted..Finding The Courage To Travel

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