Milk & Honey Magazine's travel tips for Chicago!

Chicago Travel Guide

Gina Martin

The Windy City, the city of Big Shoulders, the City that Never Sleeps

...all of these things are true about the great city of Chicago, the home of my husband and me. Many have been known to say that Chicago is the best compromise between New York and Los Angeles, and as a Chicago native, I would have to agree. There are so many wonderful places to visit on your trip to the “Second City” and I want to share some of my personal favorites with you. 


Chicago has a rich history that really began to heat up in the 1850’s. The city was officially incorporate in 1837, but had been a metropolis for the Midwest since the early 1800’s. Its location on the Great Lake Michigan proved crucial in the building of, and popularity of this great city. Despite the fire in 1871, which is rumored to have began with Mrs. O’Leary’s cows, the city rebuilt and continued to thrive. 

The only building to have survived the 1871 Great Chicago Fire... is the Water Tower building. This is located on the well known “Magnificent Mile,” which is located in the heart of the Loop (the main downtown area) on Michigan Avenue. Michigan Avenue is home to the best shopping in the city. They have many fancy shops, boutiques, and of course your traditional stores as well. There is an indoor mall, named after the historic water tower, called Water Tower Place, and then the rest of the shopping is outdoors along the always busy Michigan Avenue. 

Milk & Honey Magazine's travel tips for Chicago!

The Bean

Further South on Michigan Avenue past the shopping district, you will find the Bean. This is a landmark to the city of Chicago, and though it may seem like just a large, metallic sculpture of a bean, it is truly remarkable. The skyline reflects off of it perfectly if you catch the right angle, and your reflection can even be added to the skyline. It is a must-see if you are in town. 

The Bean is located in Millennium Park, which has ice skating in the winter, an awesome little lunch place, many free concerts in the summer, and some free group exercises. Nearby the park is the lakefront. This area has several wonderful beaches, as well as an amazing trail to run or bike or roller skate along the lake front. This would be an amazing place to watch the sunrise, or sunset as well as a phenomenal place to get a work out in!

Milk & Honey Magazine's travel tips for Chicago!

Luxury Hotels

There are plenty of options on Michigan Avenue, or nearby. The Ritz Carlton has some of the best views, and most luxurious rooms. Despite being in a hustling, bustling city the rooms create a quiet, peaceful retreat with amazing views of the lake and the skyline. There is also the Marriott located right on Michigan Avenue, which offers indoor access to a Michigan Avenue mall that contains Nordstroms and other boutiques. This is easily accessible to the best places to eat and shop. It also typically has more availability than the Ritz.

Another upscale option would be the Four Seasons, though this is slightly removed from the Michigan Avenue scene. It is extremely peaceful and comfortable. You won’t regret your stay here!! Another amazing hotel that offers some history is slightly further south on Michigan Avenue. The Hard Rock Hotel offers a luxurious, but fun atmosphere that is full of history. Additionally, the Hyatt (The Park Hyatt is directly across from the historic Water Tower, and has one of the most upscale, wonderful restaurants inside). Another phenomenal hotel is the Palmer House, located slightly off of Michigan Avenue, but near State Street, which is home to more incredible shopping and near the theater district. 

Broadway in Chicago

Broadway is a magnificent way to spend an evening. The performances are noteworthy, the architecture of the theaters is breathtaking, and the atmosphere is ideal. To me, this would be the best night out on the town. There are fantastic restaurants all around this area as well, so dinner and a show would be a great evening. 

Milk & Honey Magazine's travel tips for Chicago!

Fancy Dinner

I would suggest the 95th Signature Room. This is an exclusive restaurant on the 95th floor of the John Hancock building, which is second in height only to the Sears Tower (now referred to as the Willis Tower – but Chicago residents refuse to accept the name change). There are many other phenomenal restaurants, but this would be the most iconic in my eyes. 

Cheap Dinner

I would suggest deep dish pizza! There are many locations for these joints, but I would suggest Uno’s or Giordano’s. Gino’s East is also one of the most well-known, but it may be very difficult to get into. 

Milk & Honey Magazine's travel tips for Chicago!


Chicago is home to the Shedd Aquarium, which is my personal favorite place to go. There is also the Field Museum, the Museum of Science and Industry, the Adler Planetarium, and the Art Institute of Chicago. These are some of the best museums in the world, and I would definitely stop in one of them (or all!) on your trip to the Windy City!


If you happen to be in town on a Sunday, there are some incredible, historic churches and cathedrals in the city that are truly amazing to behold. Holy Name Cathedral is one of the most well-known churches. This is a parish that is exclusive, and always packed, but it is worthwhile to stop by just to look around at the God-inspired architecture. Additionally, Holy Family Cathedral is located near Little Italy, where you can get the most authentic Italian food (and Italian desserts!). This cathedral has the second longest aisle in the area. It also happens to be where I married my husband!

Milk & Honey Magazine's travel tips for Chicago!

If you are planning a trip to the Chicago area, feel free to contact me directly for more tourist sites, or other things to do. Also feel free to ask me any questions about the city in general!

The city has so much to offer, it may seem very overwhelming at first, but luckily there is great public transportation to help you accomplish everything you would like to get done in the time you are in town!

Enjoy your time, ladies!