Chicago is absolutely jammed packed with amazing things to see and do. From shopping, sports teams, theatre, parks, and beautiful rooftops, this city has everything you need for a great weekend getaway! Hop a quick flight into either O’Hare International Airport or Chicago Midway International Airport. This is a major hub with most cities offering direct flights at reasonable prices!

Best Times to Visit: Chicago is a year-round destination that offers visitors something different each seasons. However, if you are looking for milder weather it is best to visit in late spring, early summer, and early fall; specifically May, June, September, and October. 

Things to do:

Shop Michigan Avenue. Also known as the Magnificent Mile, this iconic fashion strip is host to the best shopping in the Windy City. It boasts more than 460 retailers, including popular brands, designer boutiques, and major department stores. Make sure to account for a shopping trip in your travel budget because this mile of shopping is enchanting.

Explore Millennium Park. Most famous for the iconic bean, Millennium Park is beautiful oasis in the middle of the city. Take in the amazing summer temperatures or ice skate underneath the bean during the winter months!

Snap a picture hanging over 110 stories. The Willis Tower (previously known as Sears Tower) is hard to miss when looking at the Chicago skyline. This tourist destination is most popular for it’s glass box jutting out over the city! Be sure to bring your camera… if you have the nerves.

Take a stroll down Riverwalk. This is especially beautiful in the summer when temperatures are warm and mild! When you hit the DuSable bridge where Michigan hits E Upper Wacker, be sure to take the steps down to the River Walk. Here, you can stroll along the river by foot, hop on a boat for one of Chicago’s many tours, or find a restaurant to stop in for a snack or drink. 

Catch a game at Wrigley Field. Wrigley is a special place no matter who you cheer for. If you’re in town for a Cubs home game, be sure to go and drink and Old Style, a true Chicago original. If no games are happening during your trip, there is plenty of entertainment exploring Wrigleyville’s restaurants and bar scene. 

Cruise on a Chicago Architecture Boat Tour. Chicago’s architecture is absolutely iconic and seeing it from the river makes it even more special. You’ll find out how Chicago grew from a small settlement into one of the world’s largest cities in less than 100 years. Don’t forget your camera!

Feature Hotels: Omni Chicago Hotel, The Drake, Hilton Chicago/Magnificent Mile Suites,

Hampton Social – enjoy an amazing brunch menu and snap a picture with the iconic “Rose all day” neon sign!

Maple & Ash – a steakhouse that is very much worth the splurge!

Quartino – if you love Italian and tapas, this is the spot for you! They also have to-go wine, which is obviously important.

Cindy’s – the best rooftop bar in the city with sweeping views of Millennium Park

Giordano’s – no trip to Chicago is complete without some famous deep dish pizza

3 Arts Cafe – located inside the Restoration Hardware offering visitors great all-day menu items