Nick and I visited Chicago for the first time about three years ago. We loved the city so much that we actually considered moving there for a little bit, but ultimately we packed up and moved to Pittsburgh (and haven't regretted our decision once!) Chicago is such a great city to visit when we have the chance. This time, the opportunity came in the form of a three day weekend and really cheap plane tickets.
If you're visiting Chicago soon, we hope our 3-day weekend travel guide will help you plan your trip! Here's our Windy City recap (and for more photos, don't forget to follow on Instagram!)
Where We Stayed
We wanted to pick a location that would be within walking distance of most places we wanted to visit, so we spent two nights at the Doubletree Hotel on the Magnificent Mile. The cost per night was surprisingly low for the location and the hotel's rating. We spend very little time in a hotel/Airbnb when we travel, so in terms of meeting our very basic needs, it was perfect! Also, the hotel had an Einstein Bros. Bagels on site, which was great for those -5° mornings.
The Magnificent Mile is basically Chicago's shopping district. There's a TON of stores, plus it's close to many attractions like the John Hancock Center, Millennium Park (home of The Bean), and Navy Pier. There are also great bars and restaurants close by, which was nice for the late nights when we walked home after dinner.
What We Ate
... Pizza, obviously! But you'll get to read all about that in a separate post (did someone say 'Pizza Tour'?) On Saturday morning we arrived pretty early, so our first stop (after coffee) was brunch at The Bongo Room in the South Loop.
Nick and I both ordered the breakfast burrito (spinach flour tortilla filled with guacamole and scrambled eggs, topped with melted jack cheese and ancho chile sour cream, salsa on the side, served with house potatoes... a mouthful, literally.) I think we both agreed that it was good, but not great. The ancho chile sour cream was delicious, but the rest of the meal was a little lacking on flavor. The description just sounded so good that we couldn't help but be a tad disappointed.
Later that evening we met up with a friend for drinks at Enolo Wine Cafe. We picked this spot at random after our first choice (Three Dots and a Dash) had a line to enter. The drinks were a little expensive, but we really enjoyed the calm atmosphere - it was great for catching up with friends and relaxing after a long day. We split a plate of truffle fries and they did not disappoint!
Sunday afternoon we took the train out to Logan Square to meet up with another friend for lunch at Chicago Diner. This vegetarian/vegan restaurant had a mouthwatering menu that made it so hard for me to order that I literally just picked a meal at random. All of our dishes were excellent (I ordered the breakfast combo while Nick and Jordan each ordered the Monte Cristo.) I can't turn down poutine when I see it on a menu, so we shared an order of their vegan poutine plate (waffle fries, Teese creamy cheddar, gravy, and green onions) - sooo good.
For drinks that day we stopped by Revolution Brewing for a beer (their brewpub is next door to Chicago Diner) and then hopped on a bus to Durkin's Bar in Lakeview to watch the Steelers game. Though the Steelers lost (:::sad face for days:::) it was awesome to watch the game at the official Steelers Nation bar of Chicago. EVERYONE had on their black and gold gear, and with IC Light bottle specials, it felt just like watching a game in the Burgh. So fun!
What We Did
Our big "event" of the trip was to visit the 360 Chicago Observatory (formerly the John Hancock Observatory) in the John Hancock tower. The observatory is on the 94th floor (1000 feet high!) and offers 360 views of the city. You're right on Lake Michigan and in the heart of downtown, so the views are truly breathtaking. We purchased "Sun and Stars" tickets so that we could visit once during the day and once at night. I'm not sure I could pick which time of day was better - I loved it all.
On our last visit we went to Skydeck Chicago in the Willis Tower and stood on "The Ledge," so we wanted to try something different this time. At the time, the Willis Tower was the tallest building in the western hemisphere, so you can imagine the crowd that draws in. The 360 Chicago Observatory in the Hancock tower was a lot more mellow and easy to enjoy. We didn't at all feel rushed or pressured to let other people in. We could have sat there all day! (They also have a bar in the observatory so we actually could have sat there all day.)
We also visited Cloud Gate (aka The Bean) in Millennium Park, the Chicago Cultural Center, the Chicago Public Library, and tracked down some colorful street art from Studio DIY's Chicago Wall Crawl (as seen in our last post.)
On our last day in town we saw Room at the theater next to our hotel because it was SO cold outside (the movie is incredible, by the way.) Then we enjoyed a few last minute slices of deep dish pizza and hopped on the train to Midway to catch our flight back to the Burgh!
We hope you enjoyed this recap of our trip! Please let us know if you have any questions (about food, things to do, transportation, anything!) and we'll answer them as best as we can. Can't wait to share our Pizza Tour with you next week!
Sarah & Nick