Chicago
Chicago is a city that we have been to twice, and each time the trip was only for 1 day. But, that being said, we have really gotten our time’s worth based on all of the cool activities we have been able to do. We went on a sunset boat tour, did The Office Experience, went to Skydeck at the Willis Tower, and most importantly, we tried as many deep dish pizzas as possible! Seriously, when we finished eating at Piquods, we walked out of the restaurant and Ubered straight to Lou Malnati’s.
Chicago is often described as a clean New York and is known as one of the top food cities in the world – we would agree with both claims. When we think about a trip to Chicago, our minds race straight towards food, but what makes Chicago such a great destination is that there is also plenty to do between meals!
Things to See and Do in Chicago
Willis Tower Exhibit
Cloud Gate
Eat Deep Dish Pizza
Sunset Boat Tour
The Office Experience
Shop Michigan Ave
“Skydeck Exhibit”
“Skydeck Exhibit”
We would like to go back to Chicago during the Summer to catch a Cubs game at Wrigley field and explore more of the city’s fantastic food scene. If we can find a good deal on the Sofitel, we would love to stay there again and just spend some time relaxing; the hotel is one of the nicest places that we’ve stayed at and there are certain times where you can get a rate so low that it almost looks like a mistake. As we mentioned, we’ve only ever been to Chicago for a day at a time, so taking some time to relax in the city would be a nice change of pace to our previous trips.
With all of the fun activities to do and great places to eat, Chicago is a perfect city for couples. This is not to say that we don’t think a family could have a great time in the city, because there are plenty of fun things to do in Chicago. Have you been to Chicago? Let us know who you think has the best deep dish pizza and what you like to do in the city!
Favorite Memory – Seeing the volcanos and learning about the indigenous culture directly from indigenous women!
Logistics
Accommodations – We have stayed at 2 really nice hotels courtesy of employer discounts – Sofitel Chicago Magnificent Mile and Hyatt Regency Chicago. There are a bunch of really nice hotels in the city so just keep an eye on the hotels you like and watch the prices.
Food – We can yap about food or just give you the cheat code here:
Breakfast – Wildberry Pancakes & Cafe
Lunch – Lou Malnati’s
Dinner Sienna Tavern
Transportation – We have done Ubers but this could really go either way. It will all depend on your itinerary. What we suggest is to plan out your trip first and then decide if your points-of-interest are within walking distance, or if you’ll need a car/Uber. Chicago is a walkable city, it just depends on what you’re doing. There are also bike rentals that you can look into if you are going to make a bunch of short trips.
Quick Tips
1
Food
See cheat code above for what to eat in Chicago.
2
Safety
Stay out of the South side. Chicago gets a bad rap for being dangerous, but it has its good and bad neighborhoods like any other big city.
3
Activity
Take a sunset boat tour! Our tour guide gave us some interesting history lessons about Chicago and cool facts about the architecture. We’re not historians or architecture people, but we were hooked! The boat route itself takes you through the Chicago River and then out to the edges of Lake Michigan where you can get amazing shots of the Chicago skyline at sunset - totally worth it!
4
Logistics
We have flown into both O’hare and Midway. O’hare is further away from downtown and a bigger airport. From what we’ve read, it is usually busier and takes longer to navigate through. If prices are similar, choose Midway. If O’hare is giving you a cheaper rate, go with O’hare.
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January 29, 2022
