Chicago is known for its chilly, windswept weather, but don’t be fooled. For much of the year, the metropolis, built on 22 miles of Lake Michigan’s southern shore, offers comfortable temperatures for outdoor enjoyment of its architectural and natural pleasures — many of which are free.
The bulk of your budget will go toward lodging, so you’ll want to be shrewd about timing your trip. Rates tend to yo-yo with the seasons (better weather brings higher prices) and business traffic (midweek rates can surge, often depending on the convention calendar). These are my top tips for ways to save in this fantastic city:
Where to stay
I like to clue friends in about lesser-known hotel options, especially those conveniently located by one of the elevated (the L) or subway train lines, such as in Old Town or Lincoln Park. One stop from Michigan Avenue’s retail-centric Magnificent Mile, the Ambassador Chicago hotel (1301 N. State Parkway) sometimes has rooms listed for $119 and up on its site, and they can appear on Hotels.com for $116 a night. HotelTonight consistently has options for $100 or less; I’ve used it to book a staycation at the Hotel Lincoln (1816 N. Clark St.), a stylish boutique lodging at the edge of Lincoln Park, for $100.
One of the most economical ways to travel around the city (and to and from its two airports), riding the L, can be its most scenic. Looping the downtown, the Brown Line weaves around skyscrapers, crosses the Chicago River and provides backyard views of many neighborhoods. Seven-day unlimited passes are $25. But the ideal way to appreciate Chicago’s renowned architecture, as well as absorb some city history, is on foot.
Things to do
Take the Must-See Chicago walking tour. Consider this 90-minute tour offered by the Chicago Architecture Center (architecture.org, 111 E. Wacker Dr.), which hits the highlights and includes admission to the center’s museum ($30 per person). It’s just off the recreational Riverwalk path, which I recommend for a twilight stroll that features postcard vistas of iconic skyscrapers.