Home to the Willis Tower, one of the tallest buildings in the western hemisphere, Chicago, Illinois flaunts one of the tallest skylines in the world. The Willis Tower stands tall in the Chicago Loop, which is the downtown area often considered the heart of all the city action. It’s in the Loop where downtown Chicago hotels provide tourists with convenient access to some of the top architectural tours in town. The architectural splendor and alluring city life invite visitors to experience the charm of the Windy City all-year round.
Those who love to shop-’til-they-drop regard the accommodations along Magnificent Mile as some of the best hotels in Chicago. These hotels in Chicago lining the famous shopping district are just steps away from the upscale shops and department stores that provide retail therapy at its finest.
Meanwhile, other visitors prefer staying overnight at Chicago hotels near the shore of Lake Michigan or at resorts with views of the Chicago and Calumet Rivers. Regardless of whether guests like to spend their vacations in towering high-rises along the Chicago skyline or in accommodations within walking distance of the famous Navy Pier, visitors can acquire cheap hotel deals in Chicago that will exceed all of their Windy City expectations.
Chicago-bound travelers who have booked their flights to Chicago through Expedia have the convenience of flying into either O’Hare International Airport or Midway International Airport. Located just 17 miles from downtown, O’Hare International Airport is one of the largest airports in the world, while Midway International Airport is only 10 miles from the Loop. Both of these airports offer ample taxi and shuffle rides servicing hotels near the airport as well as other nearby attractions and businesses. Vacationers can also pick up car rentals at these airports for the freedom of getting around at their own convenience.
Chicago is accessible from a number of major interstates, so road trippers can arrive in The Windy City by way of I-55, I-80, I-90, I-94, I-290, or I-294 depending on their starting point. Nationwide buses take these routes as well, as Greyhound features five station locations in Chicago alone.
Arriving in Chicago by train is another option. Some regard Chicago as one of the easiest cities to arrive in by train as both Amtrak and the South Shore Line service Chicago through its main hub, Union Station.
The Chicago Transit Authority (CTA) offers one of the best ways of traveling around Chicago. The CTA buses and trains offer reliable and affordable service to areas in and around the city. Commonly called the “L,” the train system is based on color-coded lines, and in order to ride, travelers must purchase transit cards at any CTA station. As for the bus, stops are generally four-blocks or so apart on major streets, and Chicago travelers can ride with preloaded money on their transit cards or with exact change. Some train and bus routes do run all night, so check the map schedules for early morning or late night transportation.
Walking in downtown is another easy way of getting around in Chicago. Although vacationers find the streets simple to navigate, those trying to drive in the Loop may face traffic and hefty parking fees. For hassle-free transportation, some prefer to hail taxis as the fares are cheaper than in other major cities.
Things to Do
One step out on the glass Willis Tower skydeck and 1,353 visible feet stand between you and the city pavement below. Place your palms on the transparent floor and watch as the city buzzes underneath your very finger tips. The Willis Tower, standing 1,450-feet tall, is the second tallest building in the United States. The granddaddy of architectural wonders, this building presents panoramic views of the Windy City, and on a clear day, views span out into the four surrounding states. A trip to the Willis Tower belongs on the very top of every Chicago travelers’ must-do list.
The sight from a gondola on the 150-foot Navy Pier Ferris Wheel is perhaps the only view in Chi-Town rivaling that of the Willis Tower. The rotating theme park ride features sweeping views of Lake Michigan and the famous city skyline. The Ferris wheel, located at the Navy Pier, was modeled after the world’s first Ferris wheel, which debuted at the Chicago 1893 World's Columbian Exposition. This ride is just one of several amusements rides in the Pier Park area of the Navy Pier, which presents some of vacationers’ favorite things to do in Chicago.
After experiencing the views from some of the top must-see attractions in Chicago, fashionistas and shopaholics may want to unwind on ground level at Magnificent Mile. This famous strip, which runs along Michigan Avenue, is a shopper’s mecca with dozens of luxury retail, designer, and department stores. The 13-block stretch is also home to some of Chicago’s finest boutique hotels, luxury five star hotels, and countless restaurants. While perusing the avenue, look up at some of the captivating and towering historic architecture, including the Wrigley Building, Chicago Water Tower, and the Tribune Tower.
Meanwhile, for those who have some additional time to explore Chicago, the Shedd Aquarium offers the perfect excursion for travelers fishing for something exciting to do on their Chicago vacation. This renowned aquarium is home to more than 25,000 fish, and is one of the largest aquariums in the entire world. The Caribbean Reef exhibit showcases moray eels and green sea turtles, while visitors can peek for anacondas and piranhas at the Amazon Rising exhibit. If the kids are in tow, a trip to the aquarium is a favorite among families visiting Chicago.
Arts & Entertainment
From Broadway hits to Lithuanian sung arias, Chicago is a crown jewel for arts and entertainment. Forget New York City, Chicago features Broadway in Chicago, which is a theater production company welcoming touring Broadway shows at five different stages scattered throughout Chi-Town, including the Bank of America Theatre, Auditorium Theatre, Ford Center for the Performing Arts Oriental Theatre, Broadway Playhouse at Water Tower Place, and the Cadillac Palace Theatre. Chicago is the place to go for stage performances as the city boasts 200 unique theatre companies.
The city of Chicago is also highly regarded for its Chicago Symphony Orchestra, said to be one of the top orchestras worldwide. The Chicago Symphony, along with the Chicago Sinfonietta, fill the halls with the bursts of trumpets and serenade of violins at the Symphony Center. Attend the Lyric Opera of Chicago at the Civic Opera House, or for an especially cultural experience, treat yourself to an opera by the Lithuanian Chicagoans at the Lithuanian Opera Company of Chicago, where the prima donna and other performers sing entirely in Lithuanian.
Before the Windy City invented Twinkies and the first drive-through banks, Native American tribes lived on the Chicago land, the Miami, Fox, and Sauk tribes, and later the Potawatomi tribe during the mid-1700s. After the Northwest Indian War, fought between the states and tribes, the Treaty of Greenville turned over the land to the U.S in 1795. By 1833, the Town of Chicago commenced, quickly growing in population with a flourishing economy, and gaining attention for its prominent political figures: Stephen Douglas and Abraham Lincoln.
1871 then marked the year of the detrimental Great Chicago Fire, which burned through the city. However, despite the damage, this disaster only proved Chicago’s resilience as the city’s reconstruction led to a bigger and better city with the introduction of the world’s first skyscraper and prominent 5 star hotels. As the city grew, The Chicago Times-Herald hosted the country’s very first automobile race in 1895, in which the winning car burned rubber at an average zooming speed of 7mph! But the city didn’t pump its brakes, Chicago continued on to invent the Twinkie in 1930, and open the country’s first drive-through bank in 1946. And Chicago has shown no signs of slowing down in modern day.
There are few things more important to Chicagoans than deep-dish pizza, and the Chicago Bears NFL team may just happen to be one of them. The Bears are Chi-Town’s pride and joy, as the NFL team leads the way with the most Pro Football Hall of Famers, the most retired jerseys, and the most regular season wins when compared to every other NFL team. However, the Chicago Blackhawks are certainly another top source of pride for the Windy City, as the NHL team has swooped down and taken five Stanley Cups back to the nest. The hockey team has soared through the years remaining one of the league’s six original teams dating back to 1926.
But the Bears and Blackhawks aren’t the only animals taking charge in Chicagoland, the Chicago Bulls have grabbed the basketball competition by the horns with six NBA championships. The Chicago Bulls became a household name during the 1980s and 90s thanks to the slam dunkin’ free throwin’ shooting guard Michael Jordan. Although Air Jordan’s return from retirement to the Bulls didn’t quite follow the fictional tale played out in the movie, “Space Jam,” in which Bugs Bunny and the gang encouraged the basketball star to return to the sport, though the return of Jordan no less benefited the team. For basketball fans vacationing in Chicago, book a 5 star hotel near the United Center and watch the Bulls charge on the court.
Immediately after the Great Chicago Fire of 1871 burned through the city, The Joseph Schlitz Brewing Company based in Milwaukee, Wisconsin, offered helped in the best way it knew how, by donating thousands of barrels of beer to the incinerated city. As the story goes, Chicago has ever since been a beer-based town, placing a special emphasis on craft brews while welcoming the establishment of breweries and pubs galore.
While the local breweries welcome beer connoisseurs alike, Chicago also features a variety of dance clubs, lounges, and live music events for those visitors really looking to paint the town red. Division Street is a one of the major strips in the city lined with the hippest clubs and best bars in the Gold Coast neighborhood. Visitors flock to this area for the hottest entertainment after the sun sets.
Sure the skydeck at the Willis Tower and the gondola rides on the Navy Pier Ferris Wheel are must-do activities during any Chicago vacation, but the true main event of every Chi-Town getaway should be eating. We’re not talking splurging on the finest dining in elegant restaurants, though these options are plentiful, but rather chowing down on the Chicago classics: hot dogs, Italian beef sandwiches, and deep-dish pizza.
There aren’t any frills when it comes to Chicago’s traditional favorites, the hot dogs are placed on poppy-seed buns and topped with relish, mustard, onions, peppers, tomatoes, and celery salt. Although vacationers may be tempted to squirt on some ketchup, don’t, as this is considered close to blasphemy in Chicago! Meanwhile, the Italian beef sandwiches are packed with thinly sliced beef dipped in broth-like gravy, and the deep-dish pizza is the city’s signature inches-thick pie baked with ingredients piled on upside down. Though these specialties define Chicago, the Windy City provides plenty of other dining options with some of the finest international cuisine found in Greektown, Little Italy, and Chinatown.
When it comes to shopping in Chicago, visitors may find themselves tempted to bring along an extra suitcase to fit all their magnificent finds on theirs cheap flights from Chicago back home. And where else to find magnificent items than Magnificent Mile itself? Vacationers who have an undeniable penchant for shopping are drawn to Mag Mile for its remarkable selection of retailers. This shopping destination is like eye candy for the shopping lover, with luxury boutiques and designers shops; it even made National Geographic’s list as one of the top shopping avenues in the world.
For some vacationing couples, nothing spells romance more than spending the day searching for treasures at the markets and then relaxing back at a romantic Chicago hotel. Fortunately, Chicago features both the Maxwell Street Market and the Randolph Street Market where shopping duos hunt for bargains, sift through antiques, and score vintage finds. Vacationers often map out their Chicago shopping trips with these markets in mind where they make unique purchases they won’t find anywhere else.
When it comes to exploring the city, navigating is quite easy when compared to other complicated city layouts. In general, blocks include roughly 100 addresses, and each block is around 1/8th of a mile. Therefore, an eight-block stretch is generally more or less one mile. With a few exceptions, most avenues run north to south, while streets run east to west. Keep these reminders in mind, and try to map out your exploration before you hit the streets. Although Chicago is considered a safe city, as is the case with any city, you’ll want to avoid looking lost or acting like an unfamiliar tourist.
Pet Friendly Travel Basics
As inviting as the city scene is with its concrete sidewalks and towering skyscrapers, it might not be a dog’s favorite playground. Fortunately, there are several doggy friendly spots in Chicago, which your furry companion will surely appreciate. For doggy paddling loving pups, the Montrose Dog Beach belongs at the top of your Chicago travel itinerary. This dog beach was Chicago’s first off-leash beach where pups can roam free. Other great spot for off-leash adventures include Grand Park Dog Park and the Winnemac Park in Lincoln Square. When traveling with your canine, just remember to book reservations at one of Chicago’s many pet friendly hotels to ensure Spot is welcome to spend the night.
Personalities & Culture
Chicago is unique in that it envelopes both the fast-paced city dwellers typical of large cities, but it also continues to indulge in the kindness and politeness of Midwestern states. There’s a hustle and bustle nature here, but the city isn’t too hurried to mind its p’s and q’s. Chicagoans tend to be polite and mild mannered, but they won’t hold back if you cross them. Your best bet for traveling in Chicago is to treat everyone with kindness, and they’ll certainly return the favor!
Keeping with its big city ways, Chicago presents a variety of culturally diverse neighborhoods as well. Make reservations at the Chicago hotels in Chinatown and expect a thriving Chinese culture, while the Belmont-Central district is home a dominating Polish community. Other cultures strongly represented in this mixing bowl include Indian, Mexican, Puerto Rican, and Vietnamese, among various others. Indulge in these cultures, explore their neighborhoods, listen to their music, and treat yourself to their cuisine to truly experience the Chicagoan culture.
Weather & Climate
Although the origin of Chicago’s nomenclature, Windy City, doesn’t actually pertain to the windy nature of this city, don’t underestimate the windiness of Chicago. The city experiences all kinds of gusts of wind from Lake Michigan during every season, from cool breezes in the summer to nose freezing bursts in winter. Chicago serves up frigid temperatures, snowflakes, and blustery winds from November through March. If you can brave the low digit temperatures, you’ll find the best discounts and cheap hotels deals in Chicago during the winter months.
For warmer temperatures and a more pleasant outdoor experience, visit Chicago any time between April and October. The spring and fall temperatures are mild, while the summer months generally bring temperatures ranging in the mid-80 degrees Fahrenheit. This time of year offers comfortable temperatures, allowing you to walk around and sightsee without bundling up. With that being said, the nights do tend to cool down, so bring layers to prepare yourself for chillier temperatures. However, throw caution to the Chicago wind when it comes to booking your getaway, as there’s plenty of entertainment to keep you busy regardless of the season in this city hot spot.
Need some more ideas for your next trip here? Our Expedia Viewfinder bloggers have recommendations for your next visit. See some of their latest blog posts below about what to eat, where to drink, what to see, and what to do.