Chicago, IL

Architectural gems and intriguing history await you in Chicago

Welcome to the Windy City! Upon arriving in Chicago, the first thing you notice is its famous skyline: the collection of iconic buildings that declare the city to be the Midwest's towering center of culture and commerce. Like all bustling metropolises, Chicago spills out across several hundred square miles, incorporating dozens of neighborhoods and several prominent suburbs, each boasting a character all its own, yet somehow still very much a part of the city as a whole.


Unforgettable Moments (Highlights)

Unlike other urban centers, Chicago gives you breathing room as well as an endless supply of things to do. You can drive to the outer points of the city, or spend your entire time within walking distance of the Loop and feel equally fulfilled. Stick to popular tourist spots and you'll see one spectacular side of the city. Dig a little deeper and you'll come across dozens of well-kept secrets, from amazing restaurants (home to several cutting-edge chefs, Chicago's grown into an internationally renowned culinary leader) to unique boutiques and museums.

Day 1 


Chicago has so much to offer that touring the city can sometimes seem like a Herculean effort, but the long walks, train rides, and cab trips are worth it for the countless culinary treats, live entertainment, and spectacular sights. And while you're at it, start a wish list of anything and everything that catches your eye - there's always the next day.



Most international flights to Chicago arrive and depart from O’Hare International Airport. To reach downtown, you can take a taxi, shuttle, or rent a taxi. Taking the CTA Blue Line trains, which run 24 hours a day, is the most affordable option. Chicago's starting points are obvious, but its destinations are infinite. Think big but start small, easing your way into this cosmopolitan, cultural mecca of the Midwest.



Take the Jackson bus east or hail a cab and begin the day with a stroll through the city's lakefront Grant Park, the crown jewel of the Chicago Park District and the perfect spot for a morning reverie. Be sure to check out the iconic Buckingham Fountain, one of the world’s largest fountains.



Chicago remains the home of the blues, so what better way to end the day than with live blues. Take a cab to B.L.U.E.S., a packed favorite of locals and tourists alike that makes a good time out of hard times. Before heading back to your place, find your way down to The Wiener's Circle for one of Chicago's famous hot dogs

Day 2 



Start your day with a visit to the Art Institute of Chicago - just north of Grant Park. This early, it shouldn't be too crowded, but plan ahead and buy tickets to avoid long lines for temporary exhibits. Be sure to check out the new Modern Wing, and if time permits, linger over lunch at Terzo Piano restaurant. To the north, its new neighbor is just as impressive. Millennium Park - part public garden, part playground - is full of remarkable and functional modern art. 

Stroll a few blocks north to Intelligentsia Coffee & Tea for a pick-me-up cup of Chicago's finest local roast. Board the 146 bus northbound on Michigan Avenue to the Addison stop, following the throngs of red- and blue-adorned Cubs fans to Wrigley Field.



At the Addison stop, brave the post-game throngs and take the Red Line train heading south back to Chicago Avenue. By foot, make your way to the original Pizzeria Uno for an authentic Chicago deep dish pie. Your stomach full, cab it to Second City, the epicenter of improv, for one of two nightly performances from the comedy troupe. The earlier show is more scripted, but the late show is followed by a bonus performance of totally improvised material.

Day 3 


Get a bird's-eye view of the city from the observation deck atop the Willis Tower (formerly Sears Tower) or the John Hancock Tower. Summer sees folks running and biking along the lakefront and brings a host of recreational activities in the city's many public parks—including playing a pick-up game of volleyball on Oak Street Beach. You can even rent a sailboat and navigate the lake for yourself.


Center of the city, the Loop offers a lesson in American urban architecture-bar none. Lined with stores, State Street is the city's original shopping thoroughfare. Spend some time exercising your credit cards in the many high-end stores along North Michigan Avenue, a.k.a. the Magnificent Mile. Since the 1960s, the Magnificent Mile, a boulevard of glitzy shops of International renown, has eclipsed the State Street.


Stroll to the trendy and upscale River North, which has garnered a reputation for its art galleries and charming bistros and boutiques. In the South Loop, recently rehabilitated Printer's Row caters to a young crowd with its coffee shops and bookstores. Treat yourself to a stellar multi-course meal—perhaps cooked by a celebrity chef—at one of the many fine dining establishments downtown.


Day 4 - Day Trip


To         MILWAUKEE

Via Car Hire or train

Duration 90 minutes each way

Today is a great day to jump on a train or hire a car to Milwaukee, a laid-back city well known for its cultural and architectural gems! You'll not find a lovelier littoral (and riverine) scene anywhere to pedal or stroll. And everyone there oozes Midwestern friendliness.



Wake up early to catch the morning train from the Union Station. If you plan to hire a car, drive along the Lake Michigan coast along WI 32 and enjoy the picturesque vistas of downtown Kenosha and pick up some Danish kringle in Racine for some great road food. Alternatively, head northwest out of Chicago and visit the Lake Geneva area and, possibly, Old World Wisconsin before cruising into the Beer City.



Feel your soul recharge as the afternoon sun illuminates your walk to the winged Santiago Calatrava addition to the Milwaukee Art Museum. After a stroll/ bike/drive north along the grand lakefront to the museums overlooking the north end atop the bluff line, it's time for lunch in the funky Brady Street area. 

Hit any outlying site tour of Miller Brewing or the Harley-Davidson museum (or, for nature/recreation-minded, a visit to the Schlitz Audubon Center) before returning downtown for a Wander through the immense Milwaukee Public Museum. If time permits, pick one of the following. Strike northward for postcard-perfect Cedarburg continue a bit farther to Port Washington. Alternatively, head northwest to Holy Hill and, later, Horicon Marsh.



At sunset, wander the Riverwalk before an early dinner at one of Milwaukee's legendary fish fries. Make sure you leave Milwaukee in time so you can catch the last train/bus back to Chicago.

Day 5 



Whether or not you have children, make a beeline for the Museum Campus to visit the John G. Shedd Aquarium, and while you're there, be sure to see the multimedia dolphin presentation. Museum Campus is also home to the Field Museum of Natural History and the Adler Planetarium. You could easily spend a day at each of these Institutions, whose exhibits, live-animal presentations, 3-D films and star shows will entertain young and old alike. 



Head next door to the Field Museum of Natural History, where you will find the famous T-Rex, Sue, and a host of other denizens of the natural world. Whether you are new to Chicago, or have lived here for years, you can always discover something new - courtesy of the Chicago Greeter program. Choose to explore one of 25 diverse neighborhoods and customize your experience with your personal areas of interest. No matter what area you choose, a knowledgeable Chicago volunteer will guide you on a two to four-hour tour via foot and public transportation. 



Take the metro to the affluent Gold Coast, most of which is preserved as a landmark historic district. Located nearby is of the city's oldest neighborhoods, Old Town. It includes an offbeat assortment of comedy clubs, shops and restaurants. Just west of Lincoln Park, gentrified Lincoln Park/DePaul encompasses an array of theaters and jazz and blues clubs, as well as a wide range of eateries. Whatever you choose, you’re guaranteed to having a fun time!

Day 6 


Considered the artistic area of Chicago, Wicker Park and Bucktown, both found along Milwaukee Avenue, present comfortable coffeehouses, alternative performance venues and unique bookshops. Just south of Milwaukee Avenue, Ukrainian Village forms the core of a small but lively Ukrainian community, distinguished by quaint ethnic shops of Chicagoans of Polish origin reside north of Logan Square.


Let’s move from Eastern Europe to Southern Europe! Located on the Near West Side, Little Italy offers a choice concentration of Italian restaurants and markets just north, the delicious aromas of Greek fare infuse the streets of Greektown. 

Navy Pier provides tons of family fun between the Ferris wheel, the Transporter FX thrill ride, the Children's Museum, and fireworks displays, no one will be bored here. Ride the Ferris wheel on Navy Pier it, then hop aboard one of the lake cruises that depart from the Pier. 



Sample the city's famous deep-dish pizza for dinner along with a midwestern prime steak at the original Morton's and a Chicago hot dog (never served with ketchup but laden with vegetables). Baseball lovers will want to eat at one of Harry Caray's two locations (33 W. Kinzie Ave., and on Navy Pier), filled with baseball memorabilia related to the late Cubs' announcer.

Day 7 

One last photo-op

Getting an evening flight out of Chicago is ideal so you can soak up every bit of the city on your last day. 

Reserve the last day only to explore the wonderful architecture this city has to offer. A mecca for those who appreciate stellar architecture, Chicago harbors a trove of skyscrapers and historic structures in its downtown core. The best way to see the highlights is to take one of the myriad tours offered by the Chicago Architecture Foundation. Whether you opt for a river cruise or a walking tour, you will loop the Loop and see the most noteworthy skyscrapers on North Michigan Avenue. Then take an excursion to Oak Park, the suburban Chicago birthplace of the Prairie School of architecture and home to the highest concentration of houses designed by the school's leader, Frank Lloyd Wright.


The Black Experience


305 E Garfield Blvd, Washington Park

Born from the vision of Chicago artist and community man Theaster Gates, the Currency Exchange Cafe is serving up real-deal hospitality on Chicago’s South Side. Operating as both storefront, cafe and events space, Executive Chef Lamar Moore has infused this casual neighborhood eatery with the home cooked, southern-inspired food you’ve been craving. Featuring great music, locally sourced art AND Back of the Yards coffee, it doesn’t really get any better than this.


203 E 75th St, Greater Grand Crossing

Original Soul is not just one of the best vegetarian restaurants in Chicago, it’s one of the best soul food spots in the city as well. How they get Tofu wings to taste just like Buffalo wings I’ll never know, but you’re definitely gonna wanna try it.


4450 N Clark St, Sheridan Park

The Black Ensemble Theater and performing arts center has been a Chicago institution for more than four decades. Founded by performing arts maven Jackie Taylor, the theater itself is prized for its original performances, outstanding productions and continued community and educational outreach programs city-wide. Their upcoming production, Hail Hail, Chuck: A Tribute to Chuck Berry, is set to wow Chicago Theater Week with a celebration of one of the greatest rock n’ roll artists of all time. You can buy your tickets here.


2748 N Lincoln Ave, Lincoln Park

Satisfy your sweet tooth at Lincoln Park’s Batter & Berries! This amazing breakfast spot was opened by Derek Rylon in 2012 and has been completely demolishing Chicago’s brunch scene ever since.


6760 S Stony Island Ave, Jackson Park Highlands

Founded by world-renown Chicago artist Theaster Gates, the Rebuild Foundation is a engine for building neighborhood community through the transformative power of performance art and cultural expression. The artists at the Foundation take spaces from within the community and re-develop them into social and cultural hubs, free programing and even housing for those that live there. Projects of the Rebuild Foundation include the Currency Exchange Cafe,  the Listening House and the Black Cinema House, all of which host a wide-array of amazing events, classes and social organizations on a weekly basis.


Multiple Locations

Trust us when we say you have not tasted great pie till you’ve visited Justice of the Pies. Though only open for catering, pre-order and pick up at the moment, owner Maya-Camille Broussard’s baking is wellll worth the wait. Whether you prefer savory or sweet, you can find Justice of the Pies goods at the Daley Plaza Farmers Market and Whole Foods Markets across the city.


1745 W North Ave, Wicker Park

Southern cooking flies North at the The Delta, a neighborhood restaurant and cocktail bar in Wicker Park. Owned and operated by veteran Chicago chef Eldridge Williams, The Delta takes its roots from his childhood home in Memphis Tennessee, focusing on the melting pot of flavors and cuisines that is the Mississippi Delta. Oh, and did we mention the drinks? ‘Cause they’re out of the world.


331 W 45th St, Fuller Park

Founded by activist, artist, dancer and all around badass Vershawn Sanders-Ward, Red Clay Dance Co. brings the art and movement of the African Diaspora to Chicago. Through both classes and performances, Sanders-Ward and her incredibly talented group of dancers aim to inspire real cultural and socio-economic change via the powers of art and expression. As if that wasn’t enough, the programs put on by Red Clay are absolutely breathtaking – you can find their full schedule here.


328 E 75th St, Greater Grand Crossing

Okay, if you somehow haven’t been to Stephanie Hart’s Brown Sugar Bakery in Greater Grand Crossing yet 1). why not???? and 2). you better get there ASAP. Boasting the tagline “dangerously delicious” Hart’s cakes and treats have been known to induce serious cravings in even the most strong willed of eaters. Stephanie has been featured on the Steve Harvey show and Food Network, meaning she’s not messing around.

I mean, just look at that cake and try to tell me you don’t wanna dig in. Oh that’s right, you can’t.

Luxury Hotels & Villas List 

Trip Prep 


Oh, logistics!

Flight costs are annoyingly unpredictable. You’ll save the most money if you book 3-6 months out. Many major attractions of Chicago are well connected by the city’s excellent network of Metro and bus. There are plenty of car hire services if you plan to venture out of the city.


Call ahead

Chicago has hundreds of amazing culinary, adventure, and cultural experiences to enjoy - it would be a shame to miss out. It’s best to book your outings and tables in advance as a steady mix of tourists and locals make this city a busy one. Want to embark on a sailing tour in Lake Michigan? Call ahead to avoid being missed out on a fun and adventurous experience.


Better safe than sorry

Although Chicago is no longer infamous for its crimes as it used to be, it’s always safer to travel with insurance. Not only does it protect personal belongings, but ensures access to expensive medical treatment should the worst happen. If you think you might take part in adventure sports make sure to check whether these are covered too.


Visa on arrival

Nationals from 37 countries, including Canada, Australia, and European Union members, are eligible to apply for Visa Waiver before 72 hours from arrival into the US. If your ESTA Application is denied, you will be required to apply for a B-1 Visitor Visa or B-2 Tourist Visa. Try to ensure you're traveling on a passport with over six months' validity and check with the US Embassy in your respective countries.

Booking Checklist 


For this itinerary, allow 6 nights, 7 days.

ARRIVE: CHICAGO (ORD) in the morning of DAY 1

DEPART: CHICAGO (ORD) in the evening of DAY 7


There are plenty of lodging options available—hotels, B&Bs, hostels—just be sure to secure your accommodation in advance. Airbnb is a great option if you are traveling as a group. (See next page for recommendations.)

Chicago, USA | DAY 1 - 7, 6 nights


Some tickets and reservations can be made 1-2 months in advance.

Transfer from airport to lodging | DAY 1

B.L.U.E.S. | DAY 1

Art Institute of Chicago | DAY 2

Train/Car hire from Chicago to Milwaukee | DAY 4

Transfer from Lodging to Airport | DAY 7

Recommended Airlines & Routes 

Direct connections to Chicago from the following cities:

North America: Vancouver, Mexico City, Montreal, Toronto, Most major US cities including Seattle, Dallas, New York, Los Angeles, Albuquerque, Atlanta, Austin, Baltimore, Las Vegas, San Francisco, Miami, Salt Lake City, Minneapolis

Europe: Zurich, Reykjavik, Dublin, Moscow, Paris, Rome, Frankfurt, London, Amsterdam, Madrid, Vienna

Asia: Beijing, New Delhi, Tokyo, Hong Kong, Istanbul, Seoul, Tel Aviv

Africa/Middle East: Amman, Dubai, Addis Ababa, Casablanca, Jeddah, Accra, Dakar, Johannesburg

Australia and Oceania: Sydney, Melbourne, Auckland

Alaska Airlines has constantly been voted as the best airlines to travel in the US with a high customer satisfaction due to entertainment options, leg room, and complimentary refreshments. Spirit and Frontier offer the most economical options. United and American Airlines have the best connectivity with international destinations.

Apps, Transportation & The ‘Gram 


Splitwise | eliminates the headache of bill splitting & a must             for group travel

Tripadvisor | a favorite resource for finding off-the-beaten-path restaurants and things to do. However, all reviews are subjective,      so don’t obsess over scores

Whatsapp | free text messaging to other Whatsapp users

NobelApp | make cheap calls locally and back home

TRANSIT BOOKING SITES | easy to use the website for finding low airfares | helpful fare prediction technology | for metro timetables and hours | Regional train timings and tickets | Uber is a popular mode of transportation in Chicago


For re-posts of your shots, @tag and use the following hashtags:

Chicago | @chicago #chicago #chicagoland #chicagofood

USA | @usatodaytravel #ustrip #usatravel

Milwaukee | @milwaukeewi #milwaukee #milwaukeewi

Travel Noire | @travelnoire #travelnoire

Destination Facts 


  • Chicago's first permanent settler — and businessman — was Jean Baptiste Point du Sable, an African-American from what is now Haiti, in 1779. In du Sable's home, which he shared with his Indian wife, the first marriage in Chicago was performed, the first election was held, and the first court handed down justice.


  • Taste of Chicago World's largest free outdoor food festival 

  • 23.5 miles. Length of Chicago's Western Avenue - the world's longest continuous street.

  • 11:30 AM - 1:30 PM LUNCH 7:00 - 10 PM DINNER


  • CHICAGO FIRSTS Mail Order Business, 1872 , Roller Skates, 1884, Steel-framed Skyscraper, 1885, Elevated Railway, 1892, Cracker Jacks, 1893, Cafeteria, 1895, Car Race, 1895, Zipper, 1896

  • Walt Disney was born in Chicago in 1901.

  • Softball, spray paint, vacuum cleaner, and “Twinkie” were invented in Chicago.

  • Chicago’s nicknames:The Windy City, The Second City, City of Big Shoulders, The City That Works.

  • The "Historic Route 66" begins in Chicago at Grant Park on Adams Street in front of the Art Institute of Chicago.

  • 110 stories: Height of the Willis Tower - the tallest building in the Western Hemisphere. It also has the world’s fastest elevators, with a top speed of 1,600 feet per minute.

  • TIPPING RULE OF THUMB: Restaurants | Tipping is a part of the culture in the US. Tip 15%-20% of the bill. Cabs | Leaving 15%-20% of the total amount is the general practice.



Getting to the airport is easy as long as you’re in Chicago. O’Hare Airport is easily accessible by city’s Metrorail from across the city. Make sure you leave at least 3 hours before your departure. You can pass the time waiting at the airport by reminiscing and looking through all of the amazing photos from your journey through Chicago.