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Transportation and Accommodations

Getting There

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.

Getting Around

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.


River North

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.

Gold Coast

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.

Lincoln Park

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.

Things to do and see

Millennium Park

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.

Movie Night in Millenium 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

The Bean

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.

Willis Tower Sky Deck

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 & Buckingham Fountain

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.

Maggie Daley Park

Public park near Grant park with playgrounds for children and an ice skating path in the winter.

Architecture Tour

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.

Chicago Riverwalk

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.

Lakeshore Path

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.

Second City

A well-known improv comedy show with a few showings per night.

Magnificent Mile

Also known as Michigan Avenue, the Magnificient Mile is located in the Gold Coast neighborhood and is a big shopping street.

Navy Pier

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.

Lincoln Park Zoo

A free zoo located just off Lake Shore Drive in Lincoln Park

Zoo Lights

Around the holidays every year, the zoo puts up lights across the property

Field Museum

A natural history museum well known for Sue the T-Rex and located on Museum Campus

Shedd Aquarium

Aquarium located on Museum Campus along Lake Michigan

Art Institute of Chicago

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

Oak Street Beach

Beach located on the Northside of the city near Lake Shore Drive, often crowded with tourists

North Avenue Beach

Beach north of Oak Street beach

River Kayaking

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

Sporting Events

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.

White Sox

Chicago’s Southside baseball team

Goose Island

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

Half Acre

Brewery with two different locations (Lincoln Brewery and Balmoral Brewery), both of which have taprooms and food service.

Revolution Brewing

Brewpub in Logan Square

Hopewell Brewing Company

Craft brewery in Logan Square

Corridor Brewery & Provisions

Cute little brewery on Southport Avenue in Chicago serving their homebrewed beers and food. They are constantly mixing up their beer flavors.

Metropolitan Brewing

Craft brewery located along the river brewing German-style beers

Old Irving Brewing Co.

Warehouse brewery with lights strung up inside, serving snacks and their beer

Taste of Chicago

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.

Chicago Air and Water Show

Free show held on an August weekend every year where pilots fly military planes and show-off fancy tricks in the sky

Food and Drink Recommendations


Summer House Santa Monica

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.

Neighborhood: Lincoln Park
Cafe Ba Ba Reeba

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.

Neighborhood: Lincoln Park
Real Good Stuff Co

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.

Neighborhoods: River North, Lakeview, West Loop, Lincoln Park, Old Town, Streeterville
3 Arts Club Cafe

Fancy dining found inside Restoration Hardware

Neighborhood: Gold Coast

Healthy restaurant with a wide assortment of options and is also known for its bakery counter (special recommendation for the Nutella filled cookie).

Neighborhoods: River North, Streeterville and Fulton Market 
Kanela Breakfast Club

Wide assortment of sweet and savory breakfast options

Neighborhoods: Wicker Park, Lakeview, Old Town, and Streeterville 

Mexican restaurant providing a good bottomless brunch meal. In the summer, there is great outdoor seating.

Neighborhood: Lakeview
Southport Grocery and Cafe

True to its name, this small restaurant on Southport sells some food items and also operates as a cafe with healthy breakfast options.

Neighborhood: Lakeview
Bakin & Eggs

Known for its bacon flight, this brunch spot is consistently a tasty brunch option

Neighborhood: Lakeview
Wheats End Cafe

Allergy-friendly brunch menu

Neighborhood: Lincoln Park

Casual brunch restaurant, often attended by Cubs fans before afternoon games

Neighborhood: Lakeview


Siena Tavern

Delicious Italian restaurant with a nice atmosphere. Be sure to make reservations in advance to secure a table.

Neighborhood: River North

Italian restaurant and wine bar

Neighborhood: River North
RPM Steak

High-end, expensive steak restaurant in downtown Chicago with fantastic food

Neighborhood: River North
RPM Italian

Sister restaurant to RPM Steak, RPM Italian offers some of the staples from RPM steak along with an Italian focused menu

Neighborhood: River North

Fancier Mexican restaurant with a nice atmosphere

Neighborhood: River North

Nice Peruvian restaurant

Neighborhood: River North

Busier Mexican restaurant with a variety of taco options

Neighborhood: River North
Cantina Laredo

Mexican restaurant

Neighborhood: River North

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.

Neighborhood: River North
Gilt Bar

Bar and restaurant serving American cuisine, with a speakeasy in the basement

Neighborhood: River North
Hub 51

American and Asian fusion restaurant with a more upbeat vibe making it a good spot for groups especially on weekend nights

Neighborhood: River North

Delicious Mediterranean restaurant

Neighborhood: River North
Hampton Social

Seafood restaurant with a Hamptons theme through its decor and atmosphere

Neighborhood: River North
Hubbard Inn

European themed restaurant and bar, which transforms into a nightclub

Neighborhood: River North
The Kitchen

American restaurant along the Chicago River

Neighborhood: River North

Fancy Asian restaurant

Neighborhood: River North

Italian restaurant

Neighborhood: River North
Gibson’s Italia

The Italian sister restaurant to Gibson’s steakhouse

Neighborhood: The Loop
Prime & Provisions

Steak restaurant

Neighborhood: The Loop
The Gage

American restaurant with an excellent burger

Neighborhood: The Loop
Beatnik on the River

Bohemian themed restaurant right along the Chicago river

Neighborhood: The Loop
Porter Kitchen & Deck

American restaurant along the Chicago River

Neighborhoods: The Loop
Green Street Smoked Meats

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.

Neighborhood: West Loop
Girl and the Goat

Famous restaurant in Chicago serving small plates

Neighborhood: West Loop

Italian restaurant with a twist, with delicious food and a great atmosphere

Neighborhood: West Loop
Bar Siena

Two-story Italian restaurant and is an easy restaurant for a night out with friends, dinner with family, or a date

Neighborhood: West Loop

Delicious Italian restaurant with small plates making it a great spot to share

Neighborhood: West Loop
La Josie

Excellent Mexican restaurant with great homemade chips, tasty margaritas, and a wide variety of taco options

Neighborhood: West Loop
Au Cheval

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.

Neighborhood: West Loop
El Che Bar

Argentinan cuisine

Neighborhood: West Loop
Lena Brava

The menu is filled with delicious seafood options with flavors inspired by Mexico’s Baja coast

Neighborhood: West Loop
Parlor Pizza Bar

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.

Neighborhood: West Loop

Tiny, cosy restaurant with excellent small plates

Neighborhood: West Loop
Twin Anchors

Small, casual and delicious barbecue restaurant

Neighborhood: Lincoln Park

Sushi restaurant

Neighborhood: Gold Coast
Chicago Q

Nicer restaurant for barbecue

Neighborhood: Old Town
Topo Gigio

Italian restaurant

Neighborhood: Old Town

Mexican restaurant open all day and good for any meal

Neighborhood: Lakeview
Ella Eli

Fancier restaurant with great ambiance and a globally inspired menu.

Neighborhood: Lakeview
Corridor Brewery and Provisions

Restaurant and brewery serving their own brewed beer, small bites, and American cuisine

Neighborhood: Lakeview
Tuco & Blondie

Mexican restaurant with outdoor patio seating

Neighborhood: Lakeview
Big Star

Mexican restaurant and bar (ID required for entry)

Neighborhoods: Wicker Park & Lakeview
Masa Azul

Gourmet Mexican cuisine with excellent drinks

Neighborhoods: Logan Square 

Cafes and Quick Bites

Stan’s Donuts

Famous donut shop

Neighborhood: Many locations   
The Doughnut Vault

Tiny shop selling a variety of donuts

Neighborhood: The Loop
Do-Rite Donuts

Serving unique flavors

Neighborhood: Various locations 
Goddess and the Baker
Swirlz Cupcakes
Neighborhood: Lincoln Park 


Sweet Mandy B’s
Neighborhood: Lincoln Park 
Molly’s Cupcakes
Neighborhood: Lincoln Park 
Bombo Bar
Neighborhood: River North 
Summer House Santa Monica
Neighborhood: Lincoln Park 
Jeni’s Ice Cream
Neighborhood: Old Town, Lakeview, Lincoln Park

Chicago Pizza

Lou Malnati’s

Rooftop Bars

Neighborhood: The Loop 
Neighborhood: The Loop
The J Parker
Neighborhood: Lincoln Park
Zed 451
Neighborhood: River North 
The Gwen
Neighborhood: River North 
The Robey (Up Room)
Neighborhood: Wicker Park
The Signature Room
Neighborhood: Gold Coast 


Blind Barber
Neighborhood: West Loop 
Neighborhood: Wicker Park 
The Violet Hour
Neighborhood: Wicker Park 
Golden Teardrops at Lonesome Rose
Three Dots and a Dash
Neighborhood: River North 
Neighborhood: River North 
Fancy Drinks
CH Distillery 
Butch McGquire’s
Halligan’s / Hooke & Ladder
Public House
The Vig
Lady McGregory’s
Old Crow
Hopsmith Tavern
City Winery

Other Notes



Transportation and Accommodations 

Things to do and see

Food and Drinks

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