Chicago, IL

Growing up in NE Indiana, Chicago was only a short drive away.  Naturally, my summers were mostly spent in the only real city in the Midwest.  This was a tradition until I recently relocated to Boston. It is, hands down, one of my favorite cities. I love this city for its stunning architecture, great good, friendly Midwestern feel, and unbeatable free summer events. Here are a few of my favorite spots and eateries for your Chicago visit.

Day 1:

• Breakfast @ Bongo Room. It's only open for breakfast and lunch. If you don't mind a short wait, the food is worth it. 
• Millenium Park. No visit to Chicago is complete until you've seen the Bean and the Jay Pritzker Pavilion.
• Grant Park. It's a short walk from Millennium Park. Have you ever seen the opening credit to Married with Children? Buckingham Fountain is right here.
• Lunch @ Giordano's. Deep dish Chicago-style pizza has a special place in my heart. 
• Navy Pier. This place is great if you have kids. For adults, there's the Landshark Beer Garden.
• Dinner @ The Purple Pig. Either go a bit early or put your name in then walk around the Magnificent Mile area. It'll work up your appetite.

Day 2:

• Lunch @ Aloha Eats. This Hawaiin eatery visit is always a must whenever I'm in the city!  Their portions are HUGE for the price.
• Cupcakes @ Molly's Cupcakes. It's right next to Aloha Eats so why not grab desserts after dinner? Try the peach cobbler cupcakes (you'll thank me later).
• North Avenue Beach. Fresh water beach! Enjoy the sun and water without the salt.
• Sunset Cruise or Architecture Cruise. 
• Dinner @ Cicchetti.
• Drinks @ Aviary. Make reservations for some of the best cocktails and food pairings.

Day 3:

• Brunch @ Flying Saucer. Cash only. It's a bit tucked away but extremely good brunch.
• Willis (Sears) Tower. Whatever you want to call it, it has a stunning view of Chicago on the skydeck. If you're daring, get on the all glass ledge.
• Shopping on the Magnificent Mile (N. Michigan Ave).
• Dinner @ Grand Lux Cafe
• Catch a show at the Chicago Theatre if you have time.
• Drinks @ The Violet Hour.

Some notes:

• The Girl & The Goat restaurant. If you're lucky enough to secure a reservation, check out Stephanie Izard's restaurant (Top Chef Season 4 winner). I'd suggest booking month(s) in advance.
• Hotels in downtown Chicago are expensive, especially during the summer months. I recommend AirBnB as a cheaper alternative.  Bonus points - the host may give you more suggestions on events, sights, eats in Chicago for your stay.