Why this Weekend get-away was one for the books!
First Things First.
Tip #1 TravelTimeIntinerary - Since Heather and I were both anxious as this was a new city we had both never traveled to, we did some research and created a timeline of attractions we 100% wanted to do. Say it with me all my OCD Travelers : Create a DESTINATION ITINERARY - Three days is no time at all to get to know and love a new city, so instead of cramming 100 things in where we were exhausted/ couldn't appreciate our time there as much, we decided on 5 or 6 places we absolutely knew we couldn't leave without doing. AND that were good for a couple, as the next time we traveled to Chicago we would have a baby with us! The simple pre-vaca organization makes each day simple, stress free and you actually get more accomplished without wasting precious vacation time debating the next thing to do. THIS IS ESPECIALLY HELPFUL WHEN TRAVELING IN LARGE GROUPS. ( SAY IT AGAIN FOR THE PEOPLE IN THE BACK ). Not to mention it also assists in the "what to wear" debacle during packing without OVERpacking - when you know where you're going you can dress accordingly and just HOW #fashionablylate you're going to be! You can google templates or just make them yourselves!
Daily Itinerary IE:
Day One Day Two ETC.
BFast Spot
Attractions
Brunch/Lunch Spot
Down Time Activity
Dinner Spot
After Hours.
THE W I N D Y CITY
“Why Chicago?"...
Because we've never been. Heather and I had a "Before Baby Bucket list" of all things we wanted to do together before we started trying to have children. That consisted of things like house renovations, sky diving ( that never was happening on my end, but it's still on this list lol) and traveling. Now, the difference here is my wife's area of expertise has been traveling around the world since she was young, now for me vacationing only happens if i have enough Xanax for the flights. So, long story short we chose one place that we both had never been to before, to check one box off the list we chose a weekend trip to Chicago!
Where Did We Stay?
“ The Peninsula| Chicago ”
Having never been to Chicago before, we broke out the American Express Fine Hotels and Resorts program to find the best place to stay. The Peninsula that is located on 108 East Superior Street was the perfect hotel location wise. It was right in the middle of the city, close to all of the shopping on Michigan Avenue and food you could ask for. I mean, Giordano's deep dish pizza was across the street, what more do you need?
Quick Tip: The Lobby , is the restaurant off the main entrance and it is fantastic! If you're waiting to check in or just need a quick bite, this is the perfect place!
The Bean (Cloud Gate) ( duh )
The Bean is the ONLY place we didn't get to see because of the weather UGH! But, this is on our list for the next time we visit!
Quick Tip: It's the highest rated spot for an Instagram photo- op!
Giordanos Pizzeria
Deep Dish Deliciousness!
PIZZA PIZZA! When you visit Chicago you HAVE to have a deep dish pie, it's just a right of passage. The infamous Giordano's was by far the most delicious and trendy place to grab a bite.
Quick Tip: You can get your pie to go! AND you can have it shipped to your home if you're feeling ChiTown Deep Dish for a Friday night
Sky Deck
103rd Floor of the Willis Tower
Thrill Seekers cannot miss this tourist attraction. SkyDeck is THE place get an unobstructed view all of Chicago morning, noon and night! And duh to get pics for instagram. The view is literally breathtaking and absolutely worth the waiting on line.
Quick Tip: You can book private breakfast, dinner or even Pop the Question!
Wrigley Field
Take me out to the Ball Game
For die-hard, season ticket holder Yankee fans, nothing compares to the Bronx Bombers, HOWEVA... #WrigleyField was everything a true baseball fan expects out of their stadium. No matter where you sit you feel like you're on the field, it was amazing. I'm someone who took some of their first steps outside my home on the field of the former Shae Stadium, so this says a lot. One must do is getting tickets to a Cubs game while you're visiting ChiTown.
Quick Tip: The only downside was getting an Uber back to hotel, leave about 20 minutes before the game ends!
BLVD.
Fine Dining for Date Night
"Retro Re-imagined" Heather and I pulled up to our fancy date night restaurant and we thought we were lost. The front is black brick with a tiny BLVD. sign. Little did we know that the decor of the restaurant was GORGEOUS. Designed to mirror the historic glamour dining scene of Sunset Boulevard the 1950s; you enter in awe to a giant chandelier. The food was fantastic so bring your appetite and dress up for date night!
Quick Tip: It's a little hard to see with the ambiance lighting, get ready to use your phone as a light to see the menu!
Bar Hopping
What more do I need to say about a pub with great drinks and amazing greasy food!
Quick Tip: They have the BEST Peach Moscow Mules!
City Shopping
Because duh
Michigan Avenue aka Magnificent Mile was flooded with all designer to popular/well-known brand name store fronts. My favorite OBVIOUSLY being the Disney store. Since Heather and I went in June it was painted in rainbow for the 50th Anniversary of the Stonewall Riots, which was a pleasant surprise. There were art installations, ice cream stores, you name it. It was the perfect way to have downtime but explore the city at the same time via an afternoon stroll!
Quick Tip: Get ready to shop and Wear Sneakers to walk around the city, it's too beautiful to pass up on because your feet are starting to hurt!
Chicago Crime Tours
If you're fascinated by old school Chicago crime stories, then the Crime Tour is def. one for you! It was about an hour and a half of the history behind Chicago's most notorious Mobsters. Everyone from John Dillinger, Bonnie and Clyde, and Al Capone were the highlights of the tour. I don't want to say too much or i'll spoil it!
Chicago Line Cruises - Boat Tours
This was Heather's favorite part of the entire vacation. The tour covered the evolution of the Chicago Skyline and the Architectural advancements and rich history it holds throughout the city.
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