Chicago: Windy City Weekend

Chicago had over 58 million visitors in 2018 according to the Chicago Tribune. With so many tourists visiting the city every year, whether you want to take it slow or cram in as much sightseeing as humanly possible, Chicago is the perfect weekend getaway! Below I will highlight a few of my favorite spots and activities that are perfect for your weekend itinerary. You probably will not be able to do all of these activities in a weekend, but hopefully, it helps inspire your Chicago getaway!

How to non-rev to Chicago

Chicago has two major airports. The biggest is O’Hare airport (ORD), which has the most international flights, and Midway (MDW) which services many domestic routes. O’Hare is a hub for both American Airlines and United Airlines while Midway is a hub for Southwest Airlines. Here’s an overview with airlines that fly non-stop to and from the main hubs. I recommend using the StaffTraveler app to find the perfect flight for you!

Don’t forget to check out our how to StaffTravel guide for some tips and tricks to the non-rev game!

Amsterdam	KLM & United Airlines
Atlanta	American Airlines, Delta Air Lines, Spirit Airlines, & Southwest Airlines
Hong Kong	Cathay Pacific & United Airlines
Delhi	Air India
Dubai	Emirates
Tokyo	All Nippon Airways, American Airlines, Japan Airlines, & United Airlines
Istanbul	Turkish Airlines
Warsaw	LOT Polish Airlines
Zurich	Swiss International Airlines
Frankfurt	Lufthansa & United Airlines
London	American Airlines, British Airways & United Airlines

Sightseeing and Shopping

Chicago Observation Deck

One of the best ways to experience the city is from one of Chicago’s many skyscrapers. To do this there are a couple of options. The city has two main observation decks: Sky Deck Chicago at the Willis Tower (formerly Sears) and 360 Chicago at the John Handcock Center. Both have excellent views of the city and both will cost you around $20. The third option is the Signature Room located on the 95th floor at the John Handcock Center. The Signature Room is an upscale restaurant and bar that offers an excellent view of the city. If you are able to keep your tab below $20 dollars then this should be the most economical option.

The Magnificent Mile

If you are a shopper you definitely should check out Chicago’s primary shopping district, the Magnificent Mile. With over a mile of upscale restaurants and shops, the Magnificent Mile is the perfect place to shop til ya drop. Be sure to check out the massive urban mall known as Chicago’s Water Tower Place. In case you are not a shopaholic no worries as the area is a great spot for photography junkies as the city’s stellar architecture is in no shortage here.

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The Chicago River Walk

Probably the best way to see Chicago’s river & lake while learning about the city is through a river cruise. The city offers architecture, sunset, and firework cruises all departing from the Chicago River Walk near the Magnificent Mile. There are also other water sports such as kayaks for rents and nice paths to enjoy a walk alongside the river.

Navy Pier

One of the biggest tourist attractions is Navy Pier. This 3,000-foot pier situated on Lake Michigan is home to restaurants, a botanical garden, and the renowned Ferris wheel. Fun fact—the first Ferris wheel was invented in Chicago in the 1893 World’s Columbian Exposition. Although the current Ferris wheel is substantially more modern, it remains a staple to the city. In addition to the Ferris wheel, Navy Pier is also where the fireworks shows are performed. As of summer 2019, fireworks are performed every Wednesday at 9:30 PM and Saturday at 10:15 PM.

North Avenue Beach

When thinking of a beach, I am guessing Chicago isn’t the first place that comes to mind. Despite no ocean access, Chicago does have some pretty nice beaches off Lake Michigan which offer great views of the city. In summer months this is a great spot to relax and even enjoy a coastal bike ride. Although winter will be far from ideal beach weather, you may be able to get some cool photos of Lake Michigan when the edges begin to freeze over.

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Nature Boardwalk at Lincoln Park Zoo

Potentially my favorite view of the Chicago Skyline is from Nature Boardwalk at Lincoln Park Zoo. Not only does this spot show an amazing view of the skyline, but it is a beautiful park with a lush green landscape. If you are familiar with NYC’s Central Park, the Nature Boardwalk gives off a fairly similar vibe.

Cloud Gate (The Bean)

Another must-see is what everyone calls the Bean. It’s a public sculpture in Chicago’s Millennium Park made of reflective stainless steel. The technical name is Cloud Gate as the sculptor intended for it to be a cloud; nonetheless, it is almost exclusively referred to as the Bean as the public believes it resembles a bean more than a cloud. The sculpture is also near one of the Chicago ice rinks so if you are in Chicago in the winter (my apologies) then that is also a cool place to check out.

Visit a Museum

Although Chicago is filled with picturesque locations, it is also a pretty cool city for museums. There is the Art Institute Museum, the Adler Planetarium, the Field Museum and my personal favorite the Museum of Science and Industry. Outside of museums the city also has the Shedd Aquarium, and two zoos, Brookfield Zoo, and Lincoln Park Zoo, which are free. Even if you are not into museums, aquariums or zoos, the area around Museum campus is one of the best views of the Chicago Skyline. It is also a great place for a picnic or even an afternoon stroll.

A picture of Harold and his girlfriend at the Lincoln Park Zoo! Taken by @navaphotogrophy

Buckingham Fountain

One of my favorite spots to shoot in Chicago, especially for the sunset is Buckingham Fountain. Sunset photography in cities can at times be challenging when the buildings block the sun rays. With the skyline situated to the West of Buckingham fountain, this makes for a great view of a sunset skyline. This is a perfect spot to relax after a fun-filled day.

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What to Eat

It is nearly impossible to go to Chicago without trying the famous pizza. When it comes to deep dish, there are a couple of options. My personal favorite is Pequod’s Pizza. With only one location in Lincoln Park, Pequod’s is often referred to as a local favorite. The downside here is it is not within walking distance from the city as it is about a 15-minute drive from the city center. If you are going for accessibility Giordano’s is a classic as well as Lou Malnati’s. Both have great deep and thin-crust pizza and have locations near each part of the city.

Where to Stay

Growing up in the Chicago suburbs, I never really had a reason to stay the night downtown. Now that I work in Dallas, I occasionally have business trips up in Chicago and always enjoy spending the night in the city. It goes without saying that there are plenty of great hotel options within the city, but personally I love hotels with central locations or a scenic view. A few of my recent favorites are Palmer House and The Robey Hotel. The Palmer House is a historic hotel with a very central location near Millennium Park and the Chicago Theatre. It is also where the tasty treat brownies were invented and yes, they do still sell delicious brownies. The Robey Hotel is located in Wicker Park which sits northwest of Downtown. It is a little bit out of the way as it is about 15 to 20 minutes from the city center, but the view is worth it! On top of the hotel is a beautiful terrace and rooftop pool which both offer excellent views of the city. In addition, Wicker Park also has a pretty solid nightlife so you should have plenty of entertainment between the epic hotel view and the bustling nightlife.

Chicago is an amazing city for a weekend or for a day trip! If you haven’t gone yet, download the StaffTraveler app to get the seat availibility for your non-rev to Chicago!