Chicago Travel Guide

Riding bikes along Lakeshore Drive

Somehow it took me until I was 29 to visit the Windy City (Fun fact: Chicago is also known as the “Second City”, it had to be rebuilt because of the Great Chicago Fire of 1871) for the first time, even though my dad is from there. I don’t know if it’s because of the brutal winters Chicago experiences and the high crime, but I had low expectations. Well….Chicago blew me away, no pun intended. My first trip was in July of 2018 and I fell in love with the city so much that I had to come back the following year for a Saints away game. Chicago is the third largest city in the US in terms of population and yet, it doesn’t have a major city vibe. It’s the GOAT of architecture – take an architecture cruise along the Chicago river; it’s located on the banks of Lake Michigan so you don’t have to go far for a beach trip; and it’s full of museums, rooftop bars, and iconic neighborhoods. If I’ve sold you, check out the Chicago travel guide I created below.

Where to Stay in Chicago:

For my first trip to Chicago I stayed at the W Chicago, which is located on the Lakeshore and is just 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 and got a 4.5-star hotel for only $150 a night! The second time I visited we stayed at the Residence Inn by Marriott Chicago Downtown for only $125 a night. Both are located in the Chicago Loop, which is the heart of the city and has a lot of the iconic attractions that I mention in this post.

Transportation in Chicago:

Do not rent a car. Chicago has very convenient public transportation and it’s also one of those cities that encourages you to walk everywhere (Pedway – A system of underground tunnels and overhead bridges that connects more than 50 buildings across 40 Chicago city blocks. You can access it at the Chicago Cultural Center’s Randolph Street lobby.) There are plenty of bike rental stations throughout the city or you can take the L Train (Short for elevated) anywhere amongst the Loop. The Loop is 1.79-miles of elevated rail that forms the hub of the Chicago “L” system. You can take the L Train from either O’Hare (blue line) or Midway (orange line) straight to the Loop for ~ $5.

What to Do in Chicago:

  • If you’re a football fan, take a tour of Soldier Field. For only $15 per person, you can see the suites, Columns, visitor’s locker room, and you can even go onto the field. FYI, you have to request a tour online first to get approved (No tours on weekends).
  • Have a panic attack standing on the Skydeck at Willis Tower. After an almost two hour wait and a 60 second elevator ride up 103 floors, you can see out 50 miles and 4 states. And if that isn’t enough of a thrill, you can stand on the Skydeck, a 4-foot section of 3-inch-thick glass that extends out from the building. It’s definitely an adrenaline rush! Especially when the kid before you keeps jumping up and down on the glass.
  • If the Skydeck isn’t your cup of tea, try the 360 Chicago Observation Deck in the John Hancock Center. Located on the 94th floor and towering 1,000 feet over the Magnificent Mile, it has floor-to-ceiling windows that allows you to see for 55 miles in any direction.
  • Take an architectural tour along the Chicago River. This is a must. Chicago has some of the most beautiful and interesting architecture that I have ever seen.
  • Rent bikes and ride 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 Field you can take amazing pics of the skyline. The bikes are $15 for a 24 hour pass and if you download the Divvy app, it’ll show you all of the bike stations where you can pick up or drop off a bike.
  • Take an obligatory selfie in front of the infamous Bean (Formally known as Cloud Gate) in Millennium Park.
  • Attend a Cubs game. 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.
  • Attend one of the city’s 67 museums – Field Museum of Natural History, Art Institute of Chicago, Chicago History Museum, Oriental Institute Museum, and Museum of Contemporary Photograph
  • Listen to Chicago jazz.
  • Laugh your ass off at the premier comedy club, The Second City.
  • Discover Chicago’s hidden garden, Caldwell Lily Pool, located in Lincoln Park.
  • Attend free Millennium Park concerts throughout the year.
  • See the historic Begin Route 66 Sign, located at the northwestern corner of Adams St. and Michigan Ave.
  • The Bean
  • Skydeck @ Willis Tower
  • Skydeck @ Willis Tower
  • Architectural Tour Along the Chicago River
  • View from Cindy’s Rooftop Bar
  • 360 Chicago Observation Deck
  • 360 Chicago Observation Deck
  • Lakeshore Drive
  • Wrigley Field
  • Chicago Theatre
  • Goose Island Brewery
  • Navy Pier
  • Harry Caray’s @ Navy Pier
  • Wrigley Field
  • Lou Malnati’s
  • Soldier Field

What to Eat & Drink in Chicago:

Tips for Visiting Chicago:

  • Chicago has a 10% base sales tax and the Loop has additional water, luxury, and liquor taxes so budget accordingly.
  • Chicago has some extreme seasons. Louisiana hot in the summer but without the humidity. And you’ve heard about their winters. It can get pretty cold even in early October so pack layers.
  • Download the Chicago CTA Transit Tracker app if you’re taking the bus or train

Bucket List for Visiting Chicago Again:

Chicago Maps: