After recently rereading the popular novel The Devil in the White City by Erik Larson, we were inspired to wax poetic about Chicago, the third-largest city in the U.S. The book is set against the backdrop of The Chicago World's Fair, which showcased Chicago's literal rise from the ashes of the Great Chicago Fire of 1871, with splendid, soaring white classical buildings (hence the name) and the world's first Ferris Wheel.
Although most of the buildings constructed for the Fair were designed to be temporary and were dismantled afterwards, Chicago's architectural reputation lives on, and her skyline includes the two tallest towers in the country: the Willis Tower and the Trump International Hotel and Tower. Inspired by this romantic image, we picked out deals for flights, hotels, and tours to make your Windy City vacation easy on the pocket, too.
Arm yourself with a copy of The Devil in the White City ($10.88 with free shipping via Prime, low by $2) for your roundtrip flight with United Airlines (from $108, a low by $49; expires March 31) to put you in the mood. Once you touch down at O'Hare International Airport, head into Chicago proper to begin experiencing the music, food, and history the city is famous for.
The Swissotel Chicago in particular is perfectly situated for an exploration of Chicago's architecture and history. The hotel is located right on the edge of Chicago's Magnificent Mile, a district in downtown Chicago that includes many of the city's most famous buildings, such as the John Hancock Center, the Trump International Hotel and Tower, the Chicago Water Tower (pictured right), and the Allerton Hotel. Plus, stays at the Swissotel start at an especially low rate of $99 a night (a low by $80; expires January 18).
You can also choose to stay on the cheap at a variety of other hotels in the area during Hotels.com's Chicago Sale (from $40 per night; expires January 31). If none of those properties spark your interest, however, you can instead stay farther south down the Mag Mile at The Silversmith Hotel & Suites (from $89 per night, a low by $69; expires February 16). Stays at this hotel come with a complimentary breakfast, which is ideal sustenance if you plan to explore the nearby Millennium Park.
Once you've got the sights, it's time to take in the sounds of Chi-town. Dig further into Chicago's history by exploring its musical past. The city made a name for itself as a swinging metropolis during the prohibition era of the roaring twenties, ripe with juggernaut characters like Louis Armstrong lighting up the jazz movement and Al Capone bootlegging liquor to keep the party hopping all night long.
This proverbial party continued into the 1940s and 1950s, when Chicago became a mecca for Blues greats like Howlin' Wolf and Buddy Guy, to name just two from a mountain of Blues heroes that were active in Chicago at the time. Immerse yourself in this rich musical history by opting for either a 2-night stay at The Hard Rock Hotel ($238, a low by $16; expires February 28), or head to the Hotel Sax Chicago ($118, a low by $14; expires January 18), which is situated next to the House of Blues Club on the Chicago River.
There's much to see in Chicago, and a tour may help you check off plenty of sights from your must-see list. An innovative and budget-friendly option is the Stray Boots Interactive Tour for two ($12, a low by $12). It's a smartphone self-guided tour that directs you around Chicago and offers scavenger hunt-style challenges, as well as tidbits of information and trivia as you go. It's also great for families because you can split up into teams and challenge each other around the city. Nothing like some friendly competition to make a vacation memorable!
We of course can't talk about Chi-town without mentioning its cuisine. Famed for its deep dish pizzas, red hots, and hot beefs, when you eat in Chicago you get your hands dirty! A lunch for two at the Michael Jordan Steakhouse ($35, a low by $18 off; expires January 20) combines Chicago food with another of the city's institutions: basketball. Named for the Chicago Bulls superstar, this restaurant has received rave reviews from several Chicago food critics and is best summed up by Cathy Pollok of Chicago magazine, who said, "Is Michael Jordan's just another steak house? Was MJ just another basketball player?"
Our bags are packed and we're ready to be transported into the world of vitality and indulgence that is Chicago. But, if you've got something different in mind for your next trip, be sure to check out our daily travel deals for other airfare, hotel, and vacation packages.
At the time of publication, these travel deals offered the lowest prices we could find. Deals may include blackout dates, additional taxes, and fees. Some of our prices may be based on mandatory double occupancy.