The Ultimate Chicago Travel Guide - From Someone Born & Raised There


So many people are visiting my beloved hometown and I love every bit of it. Here’s an authentic Chicago travel guide from someone born and raised in the Windy City. 

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

Loews Chicago O’Hare Hotel

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 

Garífuna 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 

Oak Street Beach

North Avenue Beach 

Montrose Beach

57th Street Beach 

Water Activities 

Next Wave Watersports

Festivals & Events

Chicago Blues Festival 

Chicago Restaurant Week

Black Yacht Weekend

Christkindlmarket

Do Division Street Fest

Chicago Jazz Festival

African/Caribbean International Festival of Life

Wicker Park Fest

Chicago Fashion Week

Black Women’s Expo

Chicago Women’s Expo

African Festival of the Arts

Landmarks & History

Navy Pier

Chicago Theater

Willis Tower

John Hancock Tower 

Buckingham Fountain - Downtown

Millennium Park - Downtown

Chicago Cultural Center - Downtown 

Museums & Art

Lincoln Park Zoo - Lincoln Park

The DuSable Black History Museum & Education Center 

Chicago History Museum

The Art Institute of Chicago

Shedd Aquarium

Griffin Museum of Science & Industry

Field Museum

Chicago Children’s Museum

MCA Museum of Contemporary Art

Alder Planetarium

Museum of Ice Cream

National Museum of Mexican Art - Pilsen

Rooftop

VU Rooftop Bar

ROOF on theWit

CloudBar at 360 CHICAGO

Nightlife 

Andy’s Jazz Club

Theater

Goodman Theater

Cadillac Palace Theater

Chicago Theater

Lyric Opera of Chicago

The Auditorium Theater

Chicago Symphony Orchestra

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! 

CONVERSATION

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