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As much as Max and I miss living in sunny Australia, being back in the Americas sure has a lot of benefits. For starters, we are loving how cheap it is to hop around the two continents. Airlines like Spirit make it easy and affordable to travel to Costa Rica, Peru, Colombia, and dozens of cities around the U.S. and the Caribbean. Cheap flights not only help us to explore new countries and new destinations for less, but they also allow us to visit our friends and families scattered across North America.

This year, I am particularly excited to take advantage of one of these cheap flights and plan a little ‘girl’s getaway’. It’s time to get my girlfriends out of Toronto (where they all live) and explore a new city together! We looked into a few great getaway options, but Chicago quickly emerged as the clear winner!

When to Visit

We knew that summer or fall would be the best time for a getaway to Chicago as this is when the weather in the Windy City is at its best with mostly sunny days and mild temperatures. Summer is awesome, but it’s also peak season, which typically drives up hotel and flight prices. So to help keep busting our weekend budget at bay, we’re taking advantage of affordable hotel rates and the cheapest flight fares by planning our trip for September.

Fall in Chicago. Photo by Rebecca Peplinski via Flickr CC

Where to Stay

We are still considering our options, but my initial research shows that top hotels in Chicago can be quite pricey. So we are hoping to get creative in finding a good deal on accommodations. One option is to book an IHG hotel outside of the Downtown Loop to get a bigger bang for our buck. Another is to use our credit card points to reserve a nice hotel within walking distance of Chicago’s main attractions. This would help us save on transportation costs over the weekend. The final option is Airbnb, which in the past has saved me ton of money on accommodations abroad, so it could be a great alternative for Chicago as well.

What to Do

Figuring out what to do during our time in Chicago is, in my opinion, the best part of trip planning. Luckily, there is no shortage of sights, events, and activities to keep us entertained in the city. We’ll be following the advice from the Chicago City Guide that was recently posted on our blog by a guest writer. The writer suggested that we visit Millennium Park, check out the Art Institute of Chicago, spend some time at Navy Pier, get an aerial view of the city from the Willis Tower, and enjoy Chicago’s architecture aboard Chicago’s First Lady Cruises.

Navy Pier, Chicago. Photo by Anh Dinh via Flickr CC

We are also lucky that Chicago plays host to a ton of great festivals and events in September. I definitely have my eye set on the Wine Festival and the Locally Made Festival.

What to Eat/Drink

Three words…deep dish pizza! Apparently, Lou Malnati’s Pizzeria and Giordano’s Pizza are Chicago’s biggest pizza chains specializing in this stuffed deliciousness, so that’s where we’ll be headed for one of our meals. We’ll be sure to refer to this list of 38 Essential Chicago Restaurants by the Eater for other meals. I’m also hoping to check out some of Chicago’s best vegetarian restaurants as well as the Windy City’s top vegan joints. But dragging my significant other to one of these restaurants is practically impossible. Luckily, my girlfriends share my passion for healthy plant-based alternatives.

We still have a few months to go before the trip, so fingers crossed that no other plans interfere with what’s bound to be an awesome girls trips to Chicago.

Disclaimer: This post was brought to you by InterContinental Hotels Group, but all opinions and comments are always our own.

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Planning a Girls Weekend in Chicago