I kind of feel like a dick Chicago but I had low expectations for you. Maybe because I heard about your brutal winters but in summer you’re quite lovely.
First tip for visiting Chicago: Stay Northside and as close to Lake Michigan as possible. It’s a short walk to the Navy Pier, Magnificent Mile, and plenty of restaurants and bars. I used Priceline’s Name Your Own Price for the first time. I got a 4.5 star hotel for $150 a night. We ended up staying at the W Chicago. Very hip, modern hotel. I opted against renting a car due to the expensive daily parking rate at the hotel. Don’t rent a car if you go to Chicago. You can walk, ride bikes, Uber, or take the L Train anywhere you want.
First day my dad and I took a tour of Soldier Field. It’s only $15 per person. We got to see the suites, Columns, visitor’s locker room, and we got to go onto the field. It’s worth checking out if you’re a football fan. You have to request a tour online and then you get approved (No tours on weekends). After we checked into the hotel (W was very accommodating, were able to leave our bags there and they sent us a text when our room was ready) we headed over to Willis Tower to see the Skydeck. Probably my second favorite part of the trip. After a 2 hour wait and a 60 second elevator ride up 103 floors, you can see out 50 miles and 4 states. The Sky Deck is a 4 foot section of 3 inch thick glass extending out past the building where you can step out onto and take pics. It’s definitely an adrenaline rush! Especially when the kid before you keeps jumping up and down on the glass. Later that evening we stumbled upon D4 Irish Pub for dinner. Excellent burgers and beers and good atmosphere. Me and the Pops hung out at the Hotel Bar that night for a couple drinks. If you can stomach the $14 cocktails it’s a pretty cool place to hang out and catch some live music and people watch.
The second day we did the Shoreline Architectural Tour along the Chicago River. This is a must. Chicago really does have some of the most beautiful buildings I have ever seen. Later we walked along the Magnificent Mile, which is a mile stretch of shops along Michigan Avenue. Then we headed to the park by Navy Pier and the hotel and rented bikes, $15 for a 24 hour pass. This included 30 minute rides and then anything over 30 minutes you pay a couple bucks extra. Just download the Divvy app and it’ll show you all of the bike stations you can pickup or drop off a bike. We ended up riding over 10 miles along Lakeshore Drive. It’s a great scenic tour as you get to ride along the beaches and when you’re headed back from Wrigley you can take amazing pics of the skyline. For lunch we headed to Harry Caray’s Tavern at the Pier for some nachos. Pretty cool atmosphere and full of sports memorabilia. Later that evening we walked to Millenium Park and had to check out the infamous Bean (formally known as Cloud Gate). We tried going to Lou Malnati’s for some deep dish pizza for dinner but it was a 2 hour wait. (Don’t go on a Sat evening or be prepared to wait).
Sunday was a more relaxing day and headed to The Field Museum by Soldier Field. If you’re a nerd like me and are interested in natural history you’ll get a kick out of this museum. Full of sweet dinosaur and mummy exhibits. We had tickets to the Cubs game that night so we headed out to Wrigley early. Ate some really good pizza at the HVAC Pub across the street from the ballpark. Even if you’re not a baseball fan I still think you’ll appreciate a Cubs game at Wrigley Field. The 2nd oldest MLB ballpark is nestled in the middle of a neighborhood and is full of history. Whether you have a seat in the stadium, a seat across the street on one of the rooftops, or just hang out at one of the bars along N. Clark St., you’ll have a great time.
Monday was our last day. For breakfast we went to West Egg Cafe by the hotel. We hit up an afternoon Cubs game and then for dinner we went to Broken English Taco Pub. Amazing tacos and on Tuesdays they’re $2.
I’m hoping to get back to Chicago soon. There’s still so much I want to do. Beaches along the lake. Lou Malnati’s deep dish pizza. Underground bar called The Library where you have to give a secret password to get in. Cindy’s Rooftop Bar across from Millenium Park. And brunch at The Signature Room at the top of the Hancock Building.