48 Hours in Chicago
48 Hours in Chicago
...with CTC Destination Management, a DMC Network Company
Welcome to Chicago! The bustling hub for foodies, artists, and millions of residents that call the city “home”. As the third largest city in the United States, Chicago houses a constant environment of innovation and growth. It has something for everyone—visitors flock to the populous Midwestern city to enjoy the delicious food, tour the sites frequently found in movies and TV, and get in touch with their artistic side through our many cultural institutions.
With a city that offers so much, we are glad to be your personal guide through your 48 hour taste of Chicago.
Your first taste of Chicago begins when you arrive at one of the city’s two airports—O’Hare International Airport or Midway International Airport. The first being one of the world’s busiest airports, averages 2,400 aircraft operations per day and four terminals. No worries, though! This airport, as well as Midway International Airport, are much easier to navigate with a CTC Staff member by your side. You will be greeted at the baggage claim and led directly to your car for transportation into the city.
11am: Check into Swissotel
Winding through the maze of skyscrapers, you will pull up to the Swissotel. This all glass triangular building will be the place you call home for the next 48 hours—and it’s the only property of its kind in North America! Entering the lobby, you’ll find the sleek décor and warm tones that are reflected throughout the property, especially in the recently renovated meeting space. The space was given a sleek facelift, making this property perfect for business and leisure. Alongside the modern accommodations are striking views from Millennium Park to Navy Pier. Head up to your room, steeped in the stylish sophistication of contemporary comfort. After a quick freshening up, it’s time to venture out into the city.
Your first stop is a Chicago classic—Portillo’s. With humble beginnings in Villa Park, Illinois, the chain has now grown nationwide. It serves up only the best of Chicago delicacies, including the Chicago Style Hot Dog and the always popular Italian Beef. This delicious delicacy is made with homemade Italian Beef, slow roasted for four hours and served on freshly baked French bread. The result? A sandwich as rich in flavor as it is in Chicago tradition. The casual eatery also serves up top-notch side orders and shakes, offering a little something for everyone to enjoy!
1pm: Segway Tour of Millennium Park, Maggie Daley Park, Museum Campus, and the Bean
Once you’ve had your fill at Portillo’s, head to Millennium Park and hop on a Segway for your tour! While it may seem impossible to see everything Chicago has in 48 hours, this tour gets you pretty close. Beginning in Millennium Park, you will wind through the grassy area and tree-lined pathways to Maggie Daley Park, the 2015 park addition devoting 20 acres to the public to enjoy climbing walls, a skating ribbon, picnic groves, various winding pathways, and so much more. Museum Campus is up next, taking you by the McCormick Place Convention Center, Shedd Aquarium, Soldier Field, the Field Museum of Natural History, and the Adler Planetarium—where you can catch the best view of the Chicago skyline according to local experts. Finally, you’ll come upon the infamous Chicago icon "Cloud Gate", commonly referred to as the "Bean". Snap a selfie with your charming, personable tour guide, sharing his expertise on Chicago and its sites throughout the tour. This whirlwind tour allows you to catch all the best sights as you zip through the city!
4pm: Game Room and Milk Room at Chicago Athletic Association
The nearby Chicago Athletic Association is next, just a short walk from your Segway tour and hotel. The historic building began in 1890 as a health club playground for the distinguished, and it stayed that way until hotel renovations in May 2015 transformed it into a luxury hotel open for all. Walk in and grab a drink at the exclusive cocktail lounge known as the Milk Room, allowing room for only eight guests at a time. Previously a speakeasy during prohibition, this quaint room features one of Chicago’s greatest mixologists. Combine the skill and expertise of an expert mixologist with an impressive collection of whiskey, and you can see why this space is popular with the locals!
Once you’ve had your drink, pop over to a room that is a little more active—the Game Room! Here you can try your hand at a multitude of games, including foosball, bocce, and chess. What was once the original Billiards room for the Chicago Athletic Association, is now your urban playground!
7pm: Cubs Game
From there, your next adventure is just a quick ride away on the "el", the elevated train system of Chicago. Hop off like a local at the Addison stop, and you are steps away from the historic Wrigley Field—home of the 2016 World Series Champions! As you walk the streets of the baseball centric neighborhood, you’ll see there is more than just baseball here. Throughout the area, you’ll hear live music and feel the energy of enthusiastic fans, and eventually come upon the new "Park at Wrigley", an open air plaza for fans to gather year-round. Believe it or not, there’s more to come to this area too—approximately two years’ worth of renovations and additions in the making. Walking up to the stadium, you’ll come face to face with an older icon, the Wrigley Marquee. As you enter the legendary stadium, make sure to grab a beer and Chicago Style Hot Dog, the perfect addition to any baseball game—especially in Chicago! Once you’ve settled into your seat, sit back, relax, and watch one of the nation’s top teams play America’s Favorite Pastime!
10pm: Honky-Tonk Fun
Pop into this late jazz mecca at Green Mill Jazz Club. While this legendary establishment is best known for the smooth and soulful sounds you can hear bursting from the walls, you may catch a hint of ghosts from gangster past. Hidden behind the bar, you can find a door leading to the infamous Al Capone’s secret passageway. Down these dark tunnels beneath the club are the ghostly paths, once stocked with illegal alcohol and fast getaways. Head back upstairs, and you can still slip into Capone’s booth, situated between the doors, so Capone and his henchman could keep a close eye on who came and went. Turn your eyes towards the stage, which has been home to a variety of gifted jazz musicians, including Von Freeman, Franz Jackson, and even Frank Sinatra. Though the club is still well-versed in the décor and ambiance of the 30’s and 40’s, you’ll find that presently, there is a more down-to-earth friendliness that will incite you to grab a nightcap and enjoy the sounds of Chicago’s best jazz.
8am: Goddess and Baker
Start your day off right at Goddess and Baker, where coffee rules and delightful pastries are served daily. This well-known hot spot has a superior coffee program, searching internationally for the best roasters to serve to the crowds of Chicagoans that can’t stay away. The quaint bakery also serves delicious breakfast pastries and desserts. Sip on a warm cup of coffee alongside a flakey croissant, or better yet, skip right to dessert with a colorful cookie! With its focus on delicious, seasonal flavors and mid-century style, this bakery will quickly become one of your favorites too!
9am: River Cruise/Walk
Once you’ve had your fill, head to one of the city’s most iconic locations—the Chicago River! Spanning a total of 156 miles, including the river’s many canals and branches, this winding, watery pathway provides endless options for entertainment alongside the city’s backdrop. It’s here that you will board your river cruise. This entertaining journey winds you through the city, as your personable tour guide charms you and fellow cruisers with Chicago facts, stories, and quips. Sit back and sail away as you learn about the history and architecture of the city, with skyscrapers towering over you.
11am: Food Tour
Now that you’re well-versed in Chicago by sea, it’s time for Chicago by taste! Pop over to the iconic pizzeria, Lou Malnati’s, where your flavorful tour will begin. This tour captures all of the best Chicago foods, starting with a hearty slice of deep dish pizza. This tour gives you more than a full stomach, though. It also comes equipped with a Chicago expert of food, your tour guide who shares the history of the dishes you are eating, as well as history on the city and its infamous inhabitants. This tour is sure to leave you full, winding through the River North neighborhood to stop for various iconic treats!
2pm: Broadway in Chicago
Your next stop brings you to Chicago’s more theatrical side—Broadway in Chicago! Catch a matinee of the infamous Hamilton. The musical focuses on the interesting story of Alexander Hamilton, and came to life at the hands of Lin-Manuel Miranda. The show debuted in Chicago in September 2016 and has been a hit ever since. Before its successful Chicago run, Hamilton raked in a record breaking 16 Tony nominations. Lucky for you, this award winning musical is your hot seat for the afternoon. Sit back and enjoy the show!
6pm: Dinner on Restaurant Row
After the show, you’re just a quick ride away from the foodie-scene of Chicago! Pop over to Restaurant Row in West Loop for an evening that takes fine dining to the next level. First, you’ll come to Aviary, a swanky cocktail lounge from the same group that created the world-renowned restaurant Alinea. The lounge is decked out in the sleek lounge furniture and serves creative cocktails that wouldn’t expect in a variety of forms, shapes, and sizes. Enjoy your cocktails as you munch on equally creative small bites.
After your pre-dinner drinks, head to Girl and the Goat for a dinner you’ll never forget! As the brainchild of celebrity chef Stephanie Izard, this Chicago hot-spot is a must-eat place! Walk into a warm ambiance, surrounded by warm tones and rich woods, welcoming you into the high-end eatery. Throughout the evening, you can indulge in globally influenced family-style plates that are both flavorfully creative and innovatively presented.
9pm: Chicago Helicopter Experience
Take your Chicago experience to new heights with the Chicago Helicopter Experience! Unlike any tour you’ve experienced, you’ll soar above the city, getting the unique vantage point that few can attain. Your tour begins just outside the city along the Chicago River. Here your helicopter will take flight directly towards the beautiful skyline. Passing over the city, you’ll fly over all the city sites with an unmatched aerial view. From there you’ll have the ride of the lifetime, experiencing fantastic views of Lake Michigan, Navy Pier, and the city as your pilot steers you through the skyway. This flight is sure to leave you on cloud nine!
9am: Breakfast at the Bongo Room
Start your day off right at the Bongo Room. This tasty breakfast eatery will provide with delectable dishes made from the freshest seasonal ingredients. Though the establishment founded in 1993 continuously concocts new and exciting breakfast dishes, you can always come back to find three original menu items: the Breakfast Burrito, the Croissant Sandwich, and the Vegetarian Croissant Sandwich. Combining a fun and creative menu with classics, the Bongo Room is the perfect spot to fuel your last few hours in the city.
10am: Art Institute of Chicago
Your final spot will be one of the top art institutions internationally, the Art Institute of Chicago. This attraction is easy to spot, guarded by its signature green bronze lion statues. Inside, envelope yourself in the exquisite creations of the artists on display. With nearly 300,000 works of art calling the museum home, there are multiple recognizable works. You’ll wander through multiple wings, admiring the creativity of the impressionists, enjoying the unique sculptures of Asian artists, and even venturing into the recently added Modern Wing for a glimpse at art today. As one of Chicago’s greatest cultural attractions, the Art Institute will leave you with some of Chicago’s greatest sites.
12pm: Depart Chicago
Though we are sad to see you off so soon, we know you’ll be back frequently! Chicago is a sprawling city with much to enjoy. While it’s nearly impossible to do so in 48 hours, we hope you’ve enjoyed your taste of Chicago.
One thing you would never have guessed about Chicago:
While most assume Chicago obtained the nickname "the Windy City" due to the breezy gusts coming off of Lake Michigan, the name is actually a reference to the hot air bellowing from the city’s politicians—according to local legends.
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