With a tenth wedding anniversary on the horizon but two kids and a budget at home, a friend was asking for weekend getaway ideas that would be special and fun, but wouldn't break the bank. Of course, the plan should suit the couple's unique interests...one pair's dream could be a weekend on the slopes, while another couple might prefer the beach. City or country, sophisticated or simple, energetic or relaxed, the list of options could be epic.
For a weekend, I always say it's best to keep it simple. Don't venture so far afield that you're exhausted by the journey...and don't overdo it with the schedule once you're there. There are only so many hours in the day, and you don't want to come home needing another vacation to recover!
Assuming my friends would like an urban sort of adventure, I thought Chicago could be a great escape. It's the only destination serviced by Toronto's Porter Air that takes you downtown to downtown, saving all kinds of hassle at international airports, to say nothing of expensive and time-consuming transfers to and fro. Better yet, Porter is boasting a seat sale to Chicago right now...$119 pp each way if you book before March 17.
With the budget in mind, my next stop was Hotwire, the online hotel selloff site. For dates in April, I was able to find 4.5 star accommodations (think Trump International Hotel or the Peninsula) for just over $100/night (US). Hotwire leaves a bit to chance (you don't know which hotel you're booking till you book it) but I've always had great luck. At the 4 star level and above, I'd say it's more than a safe bet.
Once you're there, Chi-town has so much to offer. Phenomenal architecture, world-class arts and culture (including stunning outdoor art), outstanding shopping, exciting sports and goooooood eats. On my next trip, I know I'm going wherever Guy Fieri went on Diners, Drive-ins and Dives!
Oprah and Obama can't be wrong, right? Chicago is my kind of town, indeed.
