Chicago Travel Guide : Exploring the Windy City

Let’s check out some some restaurants, activities and other lovely spots you should check out on your Chicago weekend trip with this travel guide.

If you’re in the Midwest, I suggest you hop in your car or a train right now and take a Chicago weekend trip.

It’s only around four hours out from Michigan and it’s definitely a great time when you go.

Let’s check out some some restaurants, activities and other lovely spots you should check out on your Chicago weekend trip with this travel guide.

Traveling to Chicago – Amtrak

This was my first time on a train and let me just say my experience was quite fun. I boarded the train around 6 a.m. on a Friday morning in Detroit.

We made a couple stops to other train locations in my state then we headed on our journey through Indiana to get to Chicago. We arrived in Chicago at around 11

Ticket Costs

$80 per person for a round trip.

Time on train

5-6 hours.


  • Food, drinks, candy available for purchase
  • Toilet room


Fairfield Inn & Suites Chicago Downtown / Magnificent Mile- 216 E Ontario St, Chicago, IL 60611

  • Perfect for being close to main attractions and Michigan Avenue.

Average price $150-200 a night.



A great way to purchase your tickets in a discount way. Adult tickets start at $114 for five attractions. Kid tickets start at $93.

Using the CityPass is a great idea because it saves money and allows you to pick many museums and attractions.

Field Museum

The Field Museum was a great time, it has so many exhibits that represent different cultures.

You can learn about the history of African Americans, Chinese culture , animals, dinosaurs and more.

Tickets start at $42 per adult for all access pass. Basic admission is $36.

Skydeck in Willis Tower

If you’re afraid of heights, you may want to sit this one out. It’s typically one of those skyline view things where you’re almost 1,000 feet in the sky looking down on Chicago.

Tickets start at $30-44 for adults.

Navy Pier

Food, drinks, rides, attractions and stores all in one. Many vendors ranging from Garrett Popcorn Shops or even a mobile Build-A-Bear Workshop store.

A great place to purchase your Chicago souvenirs.

Suggest bringing around $200-300 for activities, food and souvenirs.

Adler Planetarium

If you’re into planets and anything about space, then this planetarium is for you. It also features a 3D movie theater where you can watch films about the moon, and stars.

Tickets -$35 for adults basic admission. Kid tickets vary.

Shedd Aquarium

Shedd Aquarium

Exotic fishes and sea creatures from all over the world placed into one place. One of the largest aquariums I have ever been to and it sure tugged on my inner child.

Tickets – $39.95 for adults basic admission. Kid tickets vary.

The Art Institute of Chicago

Floors and floors of modern , contemporary art and history. Bring your walking shoes and time because this will take you a couple hours to completely finish it.

Tickets – $25 for adults and basic admission.

Food, dessert places to visit

Sugar Rush – 415 E 71st St, Chicago, IL 60619

A sweet candy shop with exotic candy bars and treats. I found a large box of Starbursts, Hello Kitty noodles and a few other delicious pieces.

Bring your funds though because this place is not cheap.

Price Range – $5-100

Sweet Mandy B’s – 254 E Ontario St, Chicago, IL 60611

A bakery in Downtown Chicago near Magnificent Mile that features cookies, cupcakes , fudge brownies and other pastries.

Price Range – $5-50

JoJo’s Shake Bar – 23 W Hubbard St, Chicago, IL 60654

A Instagram worthy milkshake joint. By now everyone has seen those exotic milkshakes that have too much candy and not enough shake.

This place also offers a variety of alcoholic milkshakes and popsicles if you want a little kick to your desert.

Price Range – $8-50

Sugar Factory – 55 E Grand Ave, Chicago, IL 60611

Known for their huge fish bowl drinks, that contain dry ice. With over 40 drinks to choose from, the Sugar Factory is one of the places you have to try.

Price Range – $10-60

Wildberry Pancakes & Cafe -130 E Randolph St, Chicago, IL 60601

A breakfast, brunch spot that is best to arrive early if you don’t want a long wait.

Breakfast basics that are quite good in taste and will fill you up.

Price range $6-20

What I wore in Chicago

In Chicago, fashion isn’t a big thing compared to places like New York or Los Angeles.

People wore causal fits, I didn’t go too crazy and wear anything that was out of the ordinary.

I kept it simple with my pleated skirts , hoodies and shorts. It was quite hot in Chicago so I wore outfits that were easy to walk in. You will be doing a lot of walking!

Ubers, Lyfts prices

I did not rent a vehicle to drive in Chicago, which meant my mom and I either walked to things or we ordered Ubers. Typically they weren’t long waits but they were pricey in areas where many attractions were or doing rush hour traffic.

Price Range – $15-40

Chicago in a nutshell

Chicago was very fun. If you’re from the Midwest it’s the coolest summer train trip to take. It’s quite expensive with their 10.25% sale tax but overall once you find those hidden gems and shop along Michigan Ave. You’ll be sad to leave.

If you’re heading to New York any time soon. Check out my recent NYC travel guide.

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