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The Maine Chick's Chicago Guide

Updated: Sep 1, 2022

We visited Chicago in July and it was such a fun trip! If you are looking for a new place to explore then I suggest you add Chicago, IL to your list. There are so many things to do such as visiting museums, shopping, sightseeing and eating delicious food.

Although there are plenty of activities to keep you busy, I would say you only need a few days to get a good sense of the city. An upside of visiting Chicago is that you can quickly get around through public transportation. Fly into Chicago O'Hare International Airport (ORD) and then catch a train directly to the heart of the city through the Chicago Transit Authority (CTA). Simple as that!

Keep reading to find out ideas on things to do, food to eat, and attractions to visit.


Things to Do:

Architecture River Boat Cruise

Something that you can't miss when visiting the city is an architecture boat cruise on the Chicago River. This was the most recommended activity by others and now I know why!

The city of Chicago has some of the most impressive architecture and it was surprisingly fascinating to learn more about it and the city's history. We did the tour in the evening so part of the boat tour was in the daylight and part of it was at night. I recommend getting an evening time slot if possible so you can experience the mesmerizing night views.

Bike Tour

Bike tours are a great way to get your bearings in a new city. We did a bike food tour through Bobby's Bike Hike and had a great time. Our tour guide, Brian, was very knowledgeable about the city's history and traditions.

We explored some neighborhoods that we probably wouldn't have gotten to see otherwise and enjoyed some of Chicago's staples such as deep-dish pizza and a Chicago hotdog.

Rent e-Bikes

If you don't want to do a bike tour, although I highly suggest it, you can also rent e-bikes at one of the many Lyft stations around the city. This option is a bit pricier, but we enjoyed it because it was our first e-bike experience and you can get around much quicker.

You can ride along the 18-mile Lakefront Trail, a paved path that provides a safe and fun way to travel for walkers, runners, and bicyclists.

Visit a Festival - 2022 Millennium Art Festival

Chicago is home to many festivals and events that celebrate food, music, culture, art, and more. Check out the event calendar to see what's happening in the city. During our visit, we visited the Millennium Art Festival where artists showcased their work on Michigan Avenue in Chicago’s Loop.

Visit a Chicago Museum - The Art Institute of Chicago

The Art Institute of Chicago is located in the heart of the city at Chicago's Grant Park and is one of the world's major museums. You can see works of art ranging from ancient European paintings and sculptures to contemporary architecture and design.

Some other museums to visit:
  • The Field Museum - A Natural History Museum that houses ancient artifacts, dino skeletons, fossils, and gems.

  • Shedd Aquarium - Showcases piranhas, frogs, snakes, turtles, predator sharks, jellies, and penguins.

  • Chicago History Museum - Commemorates the past and explores historical figures like Abraham Lincoln.

Go Shopping on the Magnificent Mile

The Magnificent Mile is Chicago’s commercial district on Michigan Avenue with upscale shops and boutiques, cool restaurants, and posh hotels. The street runs from the Chicago River up into the North Side neighborhood.


Food to Eat:

The food in Chicago didn't disappoint! We ate well during our visit, which was one of the highlights of our trip.

Chicago Deep Dish Pizza

What's a trip to Chicago without getting Chicago-style deep-dish pizza? We tried two famous Chicago pizza joints: Lou Malnati's and Giordano's. Both were delicious, but out of these two, I preferred Lou Malnati's since the crust is thinner and crispier.

Chicago deep-dish pizza tips:
  • Get a small (for 2 people) - A small pizza was more than enough for my husband and me. We couldn't finish it!

  • No need for appetizers - You do not need to order any appetizers because of how filling the pizza is. It would be a shame to fill up on apps before your pizza arrives

  • Deep-dish pizza takes time - It takes about 45 minutes to make so if you can order your pizza ahead of time.

Chicago Dogs

Another iconic food from Chicago is the Chicago Dog. Whatever you do - do not ask for ketchup! Chicago-natives will take offense since there is an extremely specific formula that already has the perfect flavor combination.

A classic Chicago-style hot dog is always made with a Vienna-Beef hot dog topped with yellow mustard, neon-green relish, freshly chopped onions, juicy red tomato wedges, a pickle spear, and a couple of pickled sport peppers on a poppy seed bun.

Brunch at Beatnik on the River

If you are looking for an Instagram-friendly restaurant to eat at then Beatnik on the River is the place to be. The restaurant has a beautiful boho chic patio overlooking the Chicago river adorned with sofas covered with cozy pillows, lush trees and plants, and tons of patterns and bright colors wherever you look.

The global-inspired menu includes appetizers, shareable plates, salads, sides, and sweets. Pictured here are the Fried Chicken and Waffles (marinated chicken thighs, preserved lemon salsa brava, turmeric waffles, Fresno pepper honey, pickled cauliflower, and cilantro), the Moroccan Pastilla (Phyllo dough, confit dates, roasted Persian pistachios, saffron, cinnamon, guinea fowl) and the Snooze Button zero-proof cocktail (cold brew coffee, salted Thai young coconut, sweetened cream). We loved everything!


Reserve your table ahead of time so you are guaranteed a river view!

Dinner at the Gilt Bar

The Gilt Bar serves upscale American classics and cocktails in a vintage library lounge. This restaurant says 'Date Night' to me because of its romantic cozy environment. We got two pasta dishes: Truffle Bucatini (fresh pasta in burgundy truffle cream sauce) and Lamb Sugo (Casarecce noodles, braised lamb, merguez).


Tourist Attractions:

Millennium Park

Something you can't miss while visiting Chicago is Millennium Park.

Admission to Millennium Park is free, and it is open daily from 6 a.m. to 11 p.m.

Cloud Gate

The most iconic tourist spot in all of Chicago is Cloud Gate, nicknamed "The bean", a sculpture that serves as the park's centerpiece. You have to get a picture in front of the attraction or a reflection of yourself through the reflective surface.

BP Pedestrian Bridge

Designed by an award-winning architect, another great photo spot is the BP bridge. The bridge links the eastern and western areas of the Park and provides great views of the surrounding area.

Lurie Garden

The 2.5-acre Lurie Garden is in the South-Eastern corner of Millennium Park. It is a tranquil place to enjoy nature and feels like the city's secret garden.

Lincoln Park Zoo and Conservatory


Lincoln Park's Zoo is home to over 200 unique species and the best part is that entry is free! There is a primate house, bird house, reptile house, penguin cove, camel, zebra, and so much more.


The Lincoln Park Conservatory provides a picturesque stroll through nature. The conservatory includes a Palm House, Fern Room, Orchid House, and Show House, which is home to annual flowers.

Note: Currently, the Conservatory is open with timed entry and adjusted hours so you will have to plan and make a reservation.

Navy Pier

Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan that has shopping, restaurants, and family attractions. You can ride up 200 feet on the Navy Pier Centennial Ferris Wheel and get a spectacular 360-degree view of the city's skyline and Lake Michigan.


General Chicago Tips:


Using the trains and buses in Chicago is the most efficient way to get around the city. Although you can buy a Ventra Card at the station, you can order one via the mail before your Chicago trip.

Ventra Cards are what you use to board CTA (trains) and Pace (buses). We recommend purchasing a multi-day pass so you can use your card unlimited times while you are there without the fear of running out of funds.

Where to Stay

It is recommended to stay north of the river. Although it might seem like the most logical choice to stay close to the Loop, which houses a lot of the tourist attractions such as Millennium Park and the Chicago Art Institute, this is primarily a business neighborhood so it becomes dead at night. Instead, opt for staying close to the Magnificent Mile (or Mag Mile for short) where the nightlife is more lively.


I know I already mentioned tours, but I wanted to reiterate how important tours are to get a full Chicago experience. The bike tour allowed us to see a lot more in less time and the boat tour was not only fun but educative. Both our tour guides gave us recommendations and ideas on what else to do in the city.

Comfy Walking Shoes

This tip goes for any city trip - make sure you bring comfortable walking shoes since you will do a lot of walking. I brought sneakers and ended up getting a blister in them which dampened my spirit so I want to repeat, bring those comfortable shoes with you!


Thanks for reading!

- The Maine Chick



Welcome to "The Maine Chick," where I celebrate all things Maine, embracing the Maine way and living life to the fullest! While you can often find me exploring my hometown of Portland, Maine, you'll also catch me traveling around the globe. Follow along!

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