Chicago – Visit the Windy City


This bustling midwest city is settled next to the beautiful Lake Michigan with towering skyscrapers, renowned museums, and world class restaurants. There is so much to do downtown and in surrounding neighborhoods, you’ll never be bored in the Windy City!

Need to Know:

Currency: USD

Language: English


ORD – O’Hare

MDW – Midway

Electrical Outlets: 120V supply voltage and 60Hz

Planning Your Trip

Accommodation – I’ve loved staying right downtown at the Blackstone. It’s a historic building which has been acquired by Marriott, so it feels boutique but you can get your hotel points.

Getting Around – I never get a car when I visit Chicago because it is easier to not have one in the city. To get from O’Hare to downtown, I usually just Uber, but you can also take the Blue Line “L” train. You can get to the blue line from Terminals 1, 2, and 3 by following the signs for “CTA Trains” or “Trains to the City.” It should cost about $5 and take about 45 mins to an hour.

Within the city, I mostly walked to took Ubers for convenience, but again you can use the “L” or the bus to get further around the city. To find the best route, I usually use Google Maps and then check the schedule on the CTA website.

City Pass – I have never bought the City Pass, but if you’re already planning to go to five attractions (Shedd Aquarium, Skydeck Chicago, Field Museum, plus two more on the list), it will save you a little money. The pass costs $114 per adult and is valid for 9 days.

Millenium Park
Jazz Showcase Chicago
Meli Brunch Chicago

Top Things to Do:

Millennium Park: Home of many of the famous icons of Chicago, swing by Millennium Park to see the “Bean” (actually called Cloud Gate), the Crown Fountain (water walls with digitized images), and the adjacent parks that make up this beautiful network of greenery in downtown Chicago.

Navy Pier: Another icon of Chicago, Navy Pier jets out into Lake Michigan with The Centennial Wheel towering over it all. Rides on the Centennial Wheel cost about $20 per person. Go explore the pier taking your time to check out the souvenir shops, try various food stands, explore the Crystal garden, and munch on some Garrett’s Popcorn.

Skydeck Chicago: For $26 you can head up to the 103rd floor of Willis Tour and step out onto the “Ledge.” Get a tingly feeling as you step on to the transparent outcroppings that place you directly above the city streets. This is a pretty cool experience and a great view of the city.

Jazz Clubs: Chicago has an amazing jazz scene and so many options to go out and enjoy. We went to Green Mill and Jazz Showcase. Green Mill is famously known for being a speakeasy during prohibition and home to the “Al Capone booth.” It was fun to go for the experience, but there was $15 cover per person that night and absolutely packed with nowhere to even comfortably stand. Once we got a seat, it was fun, but we really had to hustle for it. Jazz Showcase was a much more relaxed vibe and the stage was raised so it felt intimate from any seat in the room. 

Millenium Park
Navy Pier
Green Mill Jazz Club
Magnificent Mile: This is Chicago’s premier shopping district, home to storefronts of all your favorite brands. Spend some time shopping the luxe storefronts and checking out the famous landmarks such as the Wrigley Building, Tribune Tower, and Chicago Water Tower.
Starbucks Reserve Roastery: This four-story Starbucks experience is located on the Magnificent Mile. Come here to enjoy a classic Starbucks drink, try a tasting flight of cold brew, get a fancy pastry, grab an espresso martini, or anything else your heart desires. It is such a fun stop, I definitely recommend swinging by. 
Andersonville: If you’re looking to get out of the center of the city, try checking out this laid-back, charming area of Chicago that is known for its Swedish heritage. You have to stop at Ann Sather for breakfast and get a cinnamon roll (and when you order one you get two and they are as big as your face). After breakfast, stroll around the cute neighborhood and check out the local shops in the area.


Magnificent Mile Chicago River
Starbucks Reserve Roastery
Starbucks Magnificent Mile


Art Institute of Chicago: Located in Grant Park and home to countless works from artists such as Picasso, Monet, and Seurat, make sure to plan a visit to the Art Institute of Chicago. This art institute is commonly ranked as one of the best art museums in the world. The museum is closed on Tues and Wed, but open every other day until 5 PM with adult admission at $25 per person. 
Shedd Aquarium: For about $40 you can visit this lovely aquarium located right on Lake Michigan. I was genuinely impressed with the vast showcases of marine life as well as their focus on care and conservation. This is a fun stop for the whole family!
Field Museum of Natural History: Come see one of the largest museums of its kind showcasing natural history, animal halls, geology halls, culture halls, rotating exhibits, and more! You can spend a whole day here, but I found an afternoon to be perfect. The Field Museum is open 9 AM – 5 PM, with the last admission at 4 PM and adult tickets costing $27.


Chicago Art Institute
Field Museum
Art Institute Chicago

Restaurants We Tried in Chicago

Monteverde This is quite possibly the best restaurant I've been to in the United States. This upscale Italian restaurant is very popular so make sure you get a reservation. They also have incredible gluten free options, so this was such a great meal!
Vincent This cozy bistro up in Andersonville has amazing cocktails and a stellar menu. We enjoyed the vegetable appetizers and risotto.
Kanela Brunch Club We stopped here for brunch on our way to Navy Pier. They had strong coffee and great brunch options. It was perfect to hold us over for the day.
Meli Cafe This is brunch chain in Chicago with HUGE portions. We easily could have ordered one dish for two. I enjoyed my brunch tacos as a hearty meal for the day.
Goddess and the Baker We stopped at this nice coffee shop with a vast collection of bakery items (including a GF muffin!!) and lunch items.

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