Chicago has two airports with Ohare (ORD) being the primary airport and Midway (MDW) being the smaller option. United and American Airlines both have hubs at Chicago Ohare with a large number of flights to domestic and international destinations. Those who prefer Southwest will have to use Midway as Southwest does not fly to Ohare.
From downtown Chicago, Ohare can be reached by public transit on the blue line of the L. In rush hour, traffic from downtown to the airport can take anywhere from 45 to 90 minutes. Midway can be reached on the orange line of the L.
If traveling from towns in the midwest, trains are another option, many of which arrive and depart from Union Station.
Chicago is largely split between the North and Southside. When visiting Chicago, the Northside of the city is where you can expect to spend your time. Since Chicago is a larger city, use the L, buses, taxis, or bikes to travel between the neighborhoods. The L is an elevated transit system running throughout the city.
Located across the Chicago River from the Loop, River North is full of restaurants and bars. Unlike the Loop, which goes quiet after the work day closes, River North stays alive at night. The Loop is home to many office buildings and is the financial hub of the city. For those looking to stay in close proximity to the Loop, River North is a good option with an abundance of dining options.
One of the nicest areas in Chicago, Gold Coast is just north of River North. The Magnificient Mile, a famous stretch of Michigan Avenue, sits in the Gold Coast. This area is frequented by travelers and can be a nice place to stay when visiting Chicago.
Located further north, Lincoln Park is a neighborhood drawing in the younger generation from those just entering the workforce to young families. It is a beautiful area with a residential feel inside the city. Located about twenty minutes from downtown, it is a nice area to walk around, shop, and spend time when visiting Chicago.
Continuing North, Lakeview is another more residential area in the city where many young professionals and families live. This area is also home to the Cubs, as Wrigleyville sits inside Lakeview.
Public park on the East side of the Loop not far from Lake Michigan. The park is known for the Bean and some art exhibits including the fountains with changing faces on them. In the winter, an ice skating rink is open in the park.
In the summer, Millenium Park plays an outdoor movie every week. Grab a picnic blanket, snacks and some friends and watch a movie outside on a warm summer night in the park
An art structure called Cloud Gate, but commonly referred to as the Bean due to its shape. The surface of the structure is mirror-like and reflects the city on its west side. This is the focal point of Millenium Park.
The Willis Tower is the tallest building in Chicago with a floor at the top for visitors to observe Chicago to the North, East, South and West. The West side of the building has glass boxes off the side of the building that visitors can step into and look straight down to the ground.
Grant Park is a large, urban park between the Loop and Lake Michigan. Buckingham Fountain is located in Grant Park and the large summer music festival, Lollapalooza, takes over Grant Park every year.
Public park near Grant park with playgrounds for children and an ice skating path in the winter.
Take a boat along the Chicago River and learn about the different types of architecture used in buildings throughout the city along with the history of the city itself. There are a variety of companies offering boat tours, typically lasting around 90 minutes. This is a great way to see the city from the water. Most boats offer snacks or drinks onboard as well.
A nice path running right along the Chicago River. There are cafes, spots to grab a drink, and grassy areas to sit along the riverwalk.
The city of Chicago sits right along Lake Michigan. There is a nice running and biking path that runs for miles along the lake. It is especially nice from Lincoln Park to downtown Chicago.
A well-known improv comedy show with a few showings per night.
Also known as Michigan Avenue, the Magnificient Mile is located in the Gold Coast neighborhood and is a big shopping street.
A well-known pier along the Lake Michigan shoreline with a Ferris Wheel as its focal point. The Ferris Wheel is a smaller version of the Ferris Wheel presented at the World’s Fair in Chicago in 1893.
A free zoo located just off Lake Shore Drive in Lincoln Park
Around the holidays every year, the zoo puts up lights across the property
A natural history museum well known for Sue the T-Rex and located on Museum Campus
Aquarium located on Museum Campus along Lake Michigan
Famous art museum and one of the largest in the United States
Approximately 3-mile long elevated walking and bike path running east to west in the northwest area of Chicago
Beach located on the Northside of the city near Lake Shore Drive, often crowded with tourists
Beach north of Oak Street beach
Rent kayaks or sign-up for an organized kayaking tour where you learn about the history of Chicago and are taken along the main areas of the Chicago River
The Bears are Chicago’s football team and play at Soldier Field
The Chicago BlackHawks are the city’s hockey team. The team won three Stanley Cups in six years (2010, 2013, and 2015) after not having won a Cup in 49 years. If visiting during hockey season, attending a BlackHawks game is always a fun experience.
Chicago has two baseball teams, the Chicago Cubs and the Chicago White Sox. The Cubs are the Northside team while the Sox are the Southside team. The Chicago Cubs ballpark, Wrigley Field, is famous and sits in Wrigleyville which is an area full of bars where people hop through before and after the games.
If you cannot get tickets to a game, head over to Wrigley and watch from one of the many bars in the area. Another unique way to see the game is on one of the Wrigley rooftops; some of the buildings around Wrigley field have seats on their roof giving fans another place to watch the game.
Chicago’s Southside baseball team
There are a few different locations, with the Fulton Street location providing tastings and tours of the brewery
The taproom offers beer tastings and often has live music playing
Brewery with two different locations (Lincoln Brewery and Balmoral Brewery), both of which have taprooms and food service.
Brewpub in Logan Square
Craft brewery in Logan Square
Cute little brewery on Southport Avenue in Chicago serving their homebrewed beers and food. They are constantly mixing up their beer flavors.
Craft brewery located along the river brewing German-style beers
Warehouse brewery with lights strung up inside, serving snacks and their beer
A five-day food festival takes place in July and is held in Grant Park. It is the world’s largest food festival and includes numerous food stands along with live music.
A four-day music festival held at the beginning of August every year. Stages are spread throughout Grant Park, with artists from different genres playing from the afternoon into the night.
Free show held on an August weekend every year where pilots fly military planes and show-off fancy tricks in the sky
The restaurant has a glass roof, making for a nice vibe on a summer weekend. It is a commonly visited spot for brunch but is also open for other meals. Be sure to try the cookies sold at the front of the restaurant as they are delicious.
Excellent tapas restaurant, which diversifies its menu for brunch. It is great for dinner as well and highly recommended for a group as each person can pick a few tapas to share for the table.
This spot is known for its variety of juices but has a wider menu including brunch options like avocado toast, acai bowls, salads, and other healthy options. Some locations have a small seating area, but it is mainly used for take-away service.
Fancy dining found inside Restoration Hardware
Healthy restaurant with a wide assortment of options and is also known for its bakery counter (special recommendation for the Nutella filled cookie).
Wide assortment of sweet and savory breakfast options
Mexican restaurant providing a good bottomless brunch meal. In the summer, there is great outdoor seating.
True to its name, this small restaurant on Southport sells some food items and also operates as a cafe with healthy breakfast options.
Known for its bacon flight, this brunch spot is consistently a tasty brunch option
Allergy-friendly brunch menu
Casual brunch restaurant, often attended by Cubs fans before afternoon games
Delicious Italian restaurant with a nice atmosphere. Be sure to make reservations in advance to secure a table.
Italian restaurant and wine bar
High-end, expensive steak restaurant in downtown Chicago with fantastic food
Sister restaurant to RPM Steak, RPM Italian offers some of the staples from RPM steak along with an Italian focused menu
Fancier Mexican restaurant with a nice atmosphere
Nice Peruvian restaurant
Busier Mexican restaurant with a variety of taco options
Incredible, but pricey steak restaurant, where it is tough to get reservations. The restaurant is quite dark and holds a more romantic, date-night atmosphere.
Bar and restaurant serving American cuisine, with a speakeasy in the basement
American and Asian fusion restaurant with a more upbeat vibe making it a good spot for groups especially on weekend nights
Delicious Mediterranean restaurant
Seafood restaurant with a Hamptons theme through its decor and atmosphere
European themed restaurant and bar, which transforms into a nightclub
American restaurant along the Chicago River
Fancy Asian restaurant
The Italian sister restaurant to Gibson’s steakhouse
American restaurant with an excellent burger
Bohemian themed restaurant right along the Chicago river
American restaurant along the Chicago River
Restaurant and bar with a walk-up counter to order your choice of meats and sides. It is a great spot for an easy dinner or to meet friends for a drink. Picnic tables are up for grabs and there are lights strung throughout the restaurant.
Famous restaurant in Chicago serving small plates
Italian restaurant with a twist, with delicious food and a great atmosphere
Two-story Italian restaurant and is an easy restaurant for a night out with friends, dinner with family, or a date
Delicious Italian restaurant with small plates making it a great spot to share
Excellent Mexican restaurant with great homemade chips, tasty margaritas, and a wide variety of taco options
Possibly the most famous spot to get a burger in Chicago. It is an American diner and does not take reservations, but stop by and add your name to the list to get in the queue. On a typical Saturday, if you put your name in around 3:30 or 4:00, expect to be able to eat between 7:00 and 8:30. The burger is worth it and the duck-fat hash and fries are great additions to your meal.
The menu is filled with delicious seafood options with flavors inspired by Mexico’s Baja coast
Pizza restaurant commonly enjoyed by colleagues after work or groups of friends grabbing drinks and a bite to eat. There is a large indoor area for seating in addition to a rooftop deck.
Tiny, cosy restaurant with excellent small plates
Small, casual and delicious barbecue restaurant
Nicer restaurant for barbecue
Mexican restaurant open all day and good for any meal
Fancier restaurant with great ambiance and a globally inspired menu.
Restaurant and brewery serving their own brewed beer, small bites, and American cuisine
Mexican restaurant with outdoor patio seating
Mexican restaurant and bar (ID required for entry)
Gourmet Mexican cuisine with excellent drinks
Transportation and Accommodations
Things to do and see
Food and Drinks