Chilly Weekend in Chicago

The theme for this girls weekend trip was hot dogs and baseball!

Although it was very cold (and windy), we made the most out of our short weekend trip to Chicago with a Cubs win and lots of yummy food.

Where to Stay

I highly recommend staying downtown close to the river - it makes it easy to either walk around or hop on the train. We opted to stay at the Virgin Hotel and they upgraded us to a nice little city view! This hotel has a coffee shop, two bars (one being a rooftop bar), and an Italian restaurant.

Where to Eat

Cira - Hands down you HAVE to go and get the pistachio ravioli!! It was so good we ended up coming back for a second time! The hummus appetizer comes with warm and fluffy pita bread, and an honorable mention to the charred octopus.

The Smith - Trust me and get the truffle gnocchi and the sticky toffee pudding for dessert! Other honorable mentions are the spicy tuna crispy rice and the skirt steak.

Portillo's - Probably one of the most iconic Chicago eats! Come in for a hot dog or one of their various sandwich options.

Chicago's Dog House - they have a few locations around Chicago. We specifically went to the one in a food hall right by Millennium Park.

Cafe Deko - chef's kiss to their savory stuffed croissants!

Goddess and the Baker - YUMMY coffee options (Chicago truly lacks with matcha options) and lots of bakery items and breakfast plates to choose from! There are many locations around Chicago.

The Bandit - We did not eat here, but the food looked DELISH! This is also a great spot in West Loop to watch sports and hang out before dinner.

Things to Do

Walk around Millennium Park and get a picture at the bean!

Catch a ball game at Wrigley Field - and of course have yourself at least one hot dog!

Check out Starbucks Reserve Roastery. This place is always busy so expect long lines to order your craft drinks.

Admire the architecture as you walk around downtown. You can even take a river cruise, but we opted out due to cold and windy weather.

Things To Know Before You Go

1. Transportation is SO easy! Download the Ventra app and get a 3-day pass. You can then use Google or Apple maps to understand which lines to take to get to your destination.

2. Spring time in Chicago (if you can call it that) gives you crazy weather, so always be prepared for cold temps, wind, rain, and or sunshine!

3. For popular food spots, book weeks in advance. There are places we wanted to try (Armitage Alehouse) that were booked up even 2-weeks in advance.