How To Get There
Getting to the City of Big Shoulders depends on where you’re coming from. Chicago is the third largest city in the United States with a very major transportation system from two major airports to train systems. If you’re coming from the Midwest, driving, a train or bus ride can work. Coming from anywhere else? Plane is your best choice.
Flying
As mentioned, Chicago has two major airports. O’Hare International Airport is located in the northwest side of Chicago and Midway is located on the southwest side. O’Hare is a much larger airport and farthest from the center of the city. Midway is smaller and closer to the center of the city. Both airports are connected to the train system uniquely known as the “L”.
O’Hare operates with the Blue Line and Midway operates with the Orange Line. The Blue Line operates 24 hours but the Orange Line operates roughly from 3am to 1am. You can find more info on getting around the city using the “L” in “How to Get Around”. Choosing between O’Hare and Midway is up to you and largely can depend on where you’re staying as well as what airline you pick.
Train
Two major train systems to utilize in getting to Chicago is the Metra and the Amtrak. Downtown’s Union Station provides service for both. The Metra operates within the city and surrounding suburbs and goes out the state to Kenosha, Wisconsin.
The Amtrak is nationally connected to Chicago with major cities like Seattle, New York, Washington D.C. and the latest stop Miami making it the farthest city.
Bus
Similarly to the Amtrak, the Greyhound also connects to Chicago via other major U.S. cities. Megabus is another option along with CharterUP which is utilized within the Midwest region primarily.
Driving
Despite the obvious popularity in plane travel in our modern age, once upon a time a system like Route 66 was a popular highway to get to and from Chicago leading all the way to the west coast’s Santa Monica, California. Chicago can be accessed through several major highways and interstates like I 290 (Eisenhower), I 90 (Kennedy Expressway), and I 94 (Dan Ryan).
When to Visit
The best time of year to visit Chicago is from late March to December. There are great things to do in Chicago during the entirety of the year, but keep in mind a major factor such as the weather, the brutal winters that is. Spring and summer bring about plenty of outdoor festivals, concerts and events. Autumn offers a magnificent gaze of pumpkin spiced leaves and fall festivities. Winter in December turns the city into a winter wonderland.
Unless you’re about that winter life from January to March, I wouldn’t suggest that as the best time to visit. January brings extremely low temperatures and February is notorious for snowstorms. No matter what time you go, always be cognizant of the ever changing weather of the city of wind.
Location: Best Areas to Stay & Visit
Stay
Downtown - If you’re ready to hit the town and see the big city, downtown is a great area to stay in. Chicago’s downtown is so vast that there’s multiple areas within to choose from. Magnificent Mile is close to sights such as Lake Michigan, the Chicago River, Navy Pier, the John Hancock Tower, and of course luxury designer stores from Louis Vuitton to Chanel. River North is lush with nightlife and fine dining. The Loop is where you will discover the main Chicago landmarks like the Sears Tower (I’m a real Chicago girl, I call the Willis Tower the original name), the Chicago Theater, Millennium Park, and the famous Bean, and the Buckingham Fountain.
West Loop - The West Loop borders downtown and is rich with nightlife and a foodie paradise. Formerly apart of the west side during the days of Jane Addams, the West Loop is where you’ll find historic neighborhoods like Little Italy and Greek Town. It’s also home the University of Illinois at Chicago (UIC).
South Loop - The South Loop is still apart of downtown in my opinion. Well known spots like the Museum Campus include the Alder Planetarium, the Field Museum, and the Shedd Aquarium. The home of the Chicago Bears and a venue for large concerts, Soldier Field is there. Like the neighboring areas named above, the South Loop is also abundant in food, shopping, and day and night activities.
River North - River North is just north of Chicago’s downtown Loop area, an overwhelming location of nightlife, dining, and stores. It includes the famous luxury shopping street Magnificent Mile and is close to the main Downtown Loop area.
Streeterville - In the Near North Side region, Streeterville lies adjoining to River North. Filled with high rise condos, this location is another great spot to be as it’s close to downtown and has all of the fine dining and nightlife activities needed to revel in your trip. Streeterville also is where the famous Navy Pier is located as well as the Museum of Contemporary Art.
O’Hare Airport & Midway Airport Areas - While the O’Hare Airport and Midway Airport areas aren’t lively like other neighborhoods im Chicago, staying in these areas will guarantee full access to Chicago’s L system as both are connected. O’Hare connects to the Blue Line, Midway to the Orange.
Visit
Wicker Park - Wicker Park is where the hipsters roam. While it’s mainly a residential area, Wicker Park’s Milwaukee Avenue is overflowing with restaurants, shops, art galleries, and nightlife.
Hyde Park - Like Wicker Park, Hyde Park is also a residential area and also home to the University of Chicago. Like Wicker’s Milwaukee Avenue, Hyde Park’s 53rd Street is bustling with stores, food spots, and so much to do after hours.
Chinatown - Chinatown is Chicago’s historic neighborhood where Chinese immigrants came and settled in the 19th century. Located south of the South Loop, Chinatown is rich in culture and food with restaurants, shops, and colorful traditional Chinese architecture to explore. It’s right by the Cermak-Chinatown Red Line train stop.
Pilsen - Once occupied by Eastern European immigrants, Pilsen is one of Chicago’s main Mexican neighborhoods. There you will find authentic cuisine from Mexico and a wide array of Mexican culture such as the National Museum of Mexican Art. In more recent times, Pilsen has grown into a community for artists as well so you’re sure to find plenty of art galleries, shows, and shops to visit.
Chicagoland Suburbs
Oak Park - If you’re looking to get away from the hustle and bustle of the big city, by all means take a visit to the suburbs. Oak Park is just west of the city, bordering the west side. Oak Park is accessible via the Green Line from downtown. Downtown Oak Park’s Lake Street has numerous shops and restaurants to enjoy and there are even landmarks like the Frank Lloyd Wright home to peruse.
Evanston - Evanston is north of the city and can be accessed via the Purple Line. This quaint burb is home to Northwestern University and filled with small businesses to support.
Where to Stay
Ah. Location, location. Where you will stay in Chicago widely depends on what you’re visiting for and what you’ll be doing. Keep in mind, Chocago is a very big city and traffic plays a factor in maneuvering around. I would highly suggest staying Downtown, the West Loop, South Loop, Lincoln Park, or in the Midway or O’Hare airport areas.
Downtown
Hyatt Regency Chicago 4-star
theWit Chicago, a Hilton Hotel 4-star
The Drake 4-star
Hilton Garden Inn Chicago Downtown/Magnificent Mile 3-star
The Godfrey 4-star
Trump International Hotel & Tower 5-star
The Ritz Carlton, Chicago 5-star
Palmer House a Hilton Hotel 4-star
West Loop
Hyatt House Chicago/West Loop Fulton Market 3-star
Crowne Plaza Chicago West Loop, an IHG Hotel 4-star
Hampton Inn & Suites Chicago Medical District UIC 3-star
Midway Airport Area
Hilton Garden Inn Chicago/Midway 3-star
Courtyard Chicago Midway Airport 3-star
Hyatt Place Chicago/Midway Airport 3-star
DoubleTree by Hilton Chicago Midway Airport 3-star
Fairfield Inn & Suites Chicago Midway Airport 2-star
O’Hare Airport Area
Comfort Suites Chicago O’Hare Airport 3-star
Hilton Chicago O’Hare Airport 4-star
Hyatt Regency O’Hare Chicago 4-star
DoubleTree by Hilton Hotel Chicago O’Hare Airport Rosemont 4-star
Hampton Inn Chicago O’Hare International Airport 3-star
Miscellaneous
Hyatt Place Chicago South/University Medical Center 3-star - Hyde Park
SOPHY Hyde Park 4-star - Hyde Park
The Willows Hotel 3-star - Lincoln Park
Villa D’Citta Bed & Breakfast 4-star - Lincoln Park
The Robey 4-star - Wicker Park
Where to Eat
Short answer: everywhere. Literally everywhere. Chicago’s food scene is one of the best in the nation and in the world. There’s food from all over the globe and there’s a wide array of unique dishes created in the city. Not only will you have to unbuckle your belt and prepare for your back to increase, but you will also have to add an extra day to your itinerary to try so many iconic spots. Many of these places are personally hand picked; my favorite spots to Chicago staples frequented in my childhood and upbringing.
I’m separating this list into two parts: one part is for the legendary, must have Chicago restaurants where you can try dishes deep dish pizzas and another general list of great places to enjoy.
The Icons
Pizza
Giordano’s - multiple locations
Lou Malnati’s - multiple locations
Beggars - multiple locations
Uno Pizzeria - Streeterville, Lakeview, O’Hare
Bacci Pizza - multiple locations
Italian Beefs
Al’s #1 Italian Beef - Little Italy, Fulton River District, Logan Square, Lakeview
Burgers, Hot Dogs & Polish Sausages
The Original Maxwell Street - multiple locations
Jim’s Original - UIC area, West Lakeview
Billy Goat Tavern - Downtown (original), multiple locations
Portillo’s - River North, South Loop, Logan Square
Fatso’s Last Stand - Ukrainian Village, Sheffield Neighbors
Chicken with Mild Sauce
Uncle Remus - multiple locations
Harold’s Chicken - multiple locations
Dessert
Margie’s Candies - Bucktown, West Ravenswood
Eli’s Cheesecake - Portage Park, O’Hare
Miscellaneous
Garrett Popcorn - multiple locations
The Berghoff - Downtown
Walnut Room - Downtown
Mario’s Italian Lemonade - Little Italy
BBQ
Carson’s Ribs Prime Steaks & Famous Barbecue Chicago - Streeterville
Everything Else
Asian
Blue Sake Sushi Grill - River North, Lincoln Park
Gangnam Market - River West
Sushi Taku - Logan Square, Lincoln Park, Wicker Park
TAK Korean Bistro & Karaoke - South Loop
Soul Food
MacArthur’s Restaurant - Austin
Chicago’s Home of Chicken & Waffles - Bronzeville, Oak Park
Pearl’s Place - Bronzeville
Norman’s Bistro - Oakland
Luella’s Southern Kitchen - Lincoln Square
Soul Vibez - River North
Bronzeville Soul - Bronzeville
Mexican
Tecaclitlan Mexican Restaurant - Lincoln Park
Barcocina - West Town, Lakeview
Luxury & Fine Dining
The Gage - Downtown
Carnivale - Fulton River District
Rosebud Steakhouse - Downtown
Ralph Lauren Chicago - Magnificent Mile
American (Burgers, BBQ, etc)
Small Cheval - Fulton Market, Wicker Park, Riverside
Weber Grill Restaurant - Streeterville
Vegan & Vegetarian
Majani Soulful Vegan Cuisine - South Shore
Kale My Name - Kimball
The Chicago Diner - Logan Square, Lakeview
PLANTA Queen - River North
Soul Veg City - Auburn Park
B’Gabs & Comfort Cafe - Hyde Park
Can’t Believe It’s Not Meat - River North, Hyde Park
The Black Vegan - Little Village
Italian
Pompei - Little Italy
Canal Street Eatery and Market - West Loop
Caribbean
Kizin Creole - Rogers Park
Jerky Jerk - Tri-Taylor
GarÃfuna Flava: A Taste of Belize - Chicago Lawn
14 Parish - Hyde Park
Sweets
Stan’s Donuts - multiple locations
Ghirardelli Ice Cream & Chocolate Shop - Streeterville
Sweet Bean - South Loop
African
Demera Ethiopian Restaurant - Uptown, West Loop, Fulton Market
Ethiopian Diamond Restaurant - Edgewater
Denden Eritrean Restaurant - Rogers Park
Yassa African Restaurant - Douglas
Pacific
Aloha Wagon - Little Village
Markets
Time Out Market - Fulton Market
Chicago French Market - West Loop
Latin American
Irazu Costa Rican Restaurant - Bucktown
Brunch & Breakfast
Batter & Berries - Lakeview
Sweet Maple Cafe - Little Italy
Stax Cafe - Little Italy, River West
Molly’s Cupcakes - multiple locations
Cafes, Coffee, & Tea
Afro Joe’s Coffee & Tea - Beverly
Sip & Savor - multiple locations
Ralph's Coffee - Magnificent Mile
How to Get Around
Public Transportation
Chicago is the city for commuters, so much so that many people don’t have cars because of the transportation. The CTA (Chicago Transit Authority) bus and train system includes routes all around the city and some even run for 24 hours, every day of the week. Public transportation is especially great and beneficial when maneuvering throughout the Downtown and Loop areas as there is either barely any place to park or parking is super expensive.
Lyft & Uber
Like most places, Lyft and Uber and the good ol’ reliables when traveling. And like most places, please be aware and remember prices can surge during events and festivals and in high volume areas like a River North.
Things to Do
Chicago is the city for everyone to enjoy. No matter what age, interest, or reason, there is always something to get into in Chicago.
Beaches
Water Activities
Festivals & Events
African/Caribbean International Festival of Life
Landmarks & History
Buckingham Fountain - Downtown
Millennium Park - Downtown
Chicago Cultural Center - Downtown
Museums & Art
Lincoln Park Zoo - Lincoln Park
The DuSable Black History Museum & Education Center
Griffin Museum of Science & Industry
MCA Museum of Contemporary Art
National Museum of Mexican Art - Pilsen
Rooftop
Nightlife
Theater
TIP: You can find deals on Groupon for activities, Experiences on Airbnb, and be sure to check Eventbrite for festivals, concerts and other events.
This travel guide will be regularly updated with more tips, places, and info!
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