A Windy City Weekend: Getting Started

PrintEmailSave to Favorites

Although summer doesn’t technically end until the fall equinox on September 22, most people consider Labor Day their last summertime hoorah. Luckily, you still have some time to plan a memorable weekend getaway to celebrate the seasonal change.

While America is rife with wonderful vacation spots – from Las Vegas to Savannah – one of my all-time favorite destinations is Chicago – also lovingly known as the Windy City. As with New Orleans – one of my other favorite U.S. locales – Chicago abounds with delicious food, live music, and incredible architecture – not to mention amazing museums, award-winning theater, a thriving nightlife, and outdoor attractions galore.

I lived in the Chicago area for six marvelous years – during and after college – and now that I embrace a rather nomadic existence, I try to return whenever I can. To be fair, you could spend several weeks in Chicago and not run out of interesting diversions, but for the purposes of this post and the five-part series that will soon follow, I’m assuming that an extended weekend is all you can spare. Incidentally, Labor Day weekend is an ideal time to see Chicago, especially if you’re a music lover – the Chicago Jazz Festival, which will take place September 4-6 in Grant Park, always delivers a stupendous array of jazz performances – and all for free!

Chicago is a fascinating place to visit, especially if you have children and/or plan to stick to a reasonable budget. Getting there is fairly easy – since it sits at the convergence of several interstates (I-55, I-57, I-88, I-90, and I-94) and serves as a main hub for both airlines (at O’Hare International Airport and Midway International Airport) and trains (via Amtrak for long-distance travelers and Metra for in-state vacationers). Getting around is even easier, thanks to the extensive Chicago Transit Authority (CTA) system – upon which I frequently relied during my carefree, budget-conscious college days. For $5.75, you can purchase a one-day pass, which allows you unlimited access to CTA busses and rail lines – an utter bargain, when you consider just how efficiently you’ll be able to traverse the city. Of course, if you’re visiting Chicago during an extended holiday weekend, the three-day pass, which costs $14, is an even better deal.

Because the Chicagoland area is so well connected, you can pretty much book a hotel anywhere – and still be able to tour the city. The last time my husband and I were in town, we stayed at the reasonably priced Inn at Lincoln Park (601 W. Diversey Pkwy., 866/774-7275, $100-160 d), a clean, centrally located hotel that even offers inexpensive parking – a must-have in a crowded metropolis like Chicago.

Now, if you do plan to head to Chicago for an extended weekend, you’ll want to get the most out of your brief stay. To that end, I’ve decided to explore the Windy City in a bit more depth than one mere post can accommodate. So, over the next five days, I’ll be posting the rest of this six-part series, which will cover my top picks for the city’s museums, eateries, outdoor activities, and other diversions. Then, perhaps, you’ll come to love Chicago as much as I do.

For more information about Chicago’s events and accommodations, as well as other travel tips, consult Explore Chicago, the city’s official tourism site, or contact the Chicago Convention & Tourism Bureau (312/567-8500).

-----

As always, I’m open to ideas for future posts. If you have any suggestions, burning questions, or destinations that you’d like me to explore in greater detail, please comment below or contact me at laura [at] wanderingsoles [dot] com.