The first city guide in our #WhereIStay series? Chicago, of course. Brittany from our marketing team dishes out her favorite spots in the Windy City, sans tourist traps. Check out her guide then don’t forget to share your own travel tips with us using #WhereIStay for the chance to win big prizes!
Where to Eat in Chicago
- Skip the deep dish and head north to Ravenswood for the cities best pie. I love Spacca Napoli for their authentic wood-fired ‘za straight from the VPN approved oven. Not to mention, the insanely creamy burrata.
- The Mexican style prawns doused in marinade at Veneno de Nayarit are not to be missed. Don’t be afraid to get your hands dirty.
- Enjoy the best fried chicken north of the Mason Dixie line at Roost Carolina Kitchen. Fluffy biscuits with honey and savory bread pudding round out an epic meal.
- Chicago French Market: You’ll find something for everyone at this gourmet food market right outside the West Loop. My favorites are:
- Aloha Poke: Poke craze is in full swing in Chicago. This is my go to – their fish is super fresh and I love that I can add unlimited toppings (tobiko, mango, and edamame are my favorites!)
- Pastoral: The best place to grab cheese, charcuterie, and wine for a picnic at Millenium park. In the summer, I love to do movies in the park nights with friends.
- Beaver Donuts: Mini donuts with serious flavor. Start with plain donuts then you add your own toppings. My custom combination is nutella with strawberry jam.
What to See & Do in Chicago
- Grab a pre-dinner drink at Londonhouse for sweeping views of the Chicago river.
- Hit the 606, the cities newest urban walking trail which cuts through Bucktown and Wicker Park.
- Try a sunset sail on Lake Michigan for the best view of the city skyline. If you are feeling even more adventurous, opt for a helicopter tour of the city.
- Grab bleacher seats for a Cubs game, even if you aren’t a huge fan of baseball. It’s the only place in town for you to get infamous Hot Doug’s sausages since the namesake restaurant closed.
Where to Stay in Chicago
- PUBLIC Chicago: Check out the brunch at the hotel restaurant, Pump Room.
- Mile North Chicago: Great city views from the rooftop lounge
- dana hotel and spa: Award winning spa (ranked on Conde Nast’s Top 100) and incredible location minutes from the Magnificent Mile.
Keep following our stories and travel guides on social media (Instagram, Facebook, Twitter, Pinterest) and learn more about how we travel and where we stay. Then, tell us your own story using #WhereIStay for the chance to win big prizes, including a grand prizes of $500 in travel credits plus an exclusive travelers kit curated by the Stayful team. We’ll announce the winners on August 31.