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A Dame Traveler Insider Guide To Chicago

‘My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.’ – Oprah Winfrey

8 years ago, I took a leap of faith and left everything I’ve ever known in the suburbs of Michigan where I grew up, to start a new life in the city of Chicago. At the age of 20, coming from a strict Middle Eastern family, this was no small feat. I was on my own financially, emotionally and mentally, and pushed my way through obtaining a Bachelor’s of Science in Nursing at the Loyola University Chicago’s nursing school, successfully graduated and got got a job. I’ve traveled all over the world but whenever my plane lands in Chicago, my heart flutters and I’m reminded again and again why I love this city so much.

Sadly, I said farewell to Chicago to move to New York City in 2016 which was bittersweet time for me but Chicago will always be one of the most beautiful and special cities in the world in my eyes so I’d like to share this i guide with you all to encourage you to visit this incredible, underrated city.

Stunning architecture, friendly locals, gorgeous Lake Michigan, tons of speakeasys, world class restaurants and more, Chicago truly has something for everyone.

Things to do

Take a helicopter ride

There are so many viewpoints of Chicago’s stunning skyline but the best is surely from a helicopter. Chicago Helicopter Experiences Tours took us on a 20 minute ride over the city during twilight hour and it was pretty incredibly to watch the sky turn pink and the sun sink down. Hands down, one of my best Chicago memories to date!

Visit during Springtime

Located in the Midwest, Chicago is home to all four seasons in all of their glory but Springtime in Chicago is super special as the city defrosts from the cold winter and blooms beautifully. Michigan Avenue is covered in blankets of tulips and flowering trees hover over Grant Park. It’s truly a sight to see!

Experience Summertime Chi

Chicago is one of the best places to visit during Summertime- the lake, the outdoor dining, the beautiful sunsets, rooftops and more. The energy is amazing and there is so much to do.

Skydeck Chicago

There is no shortage of epic views in Chicago but one of the coolest is from the Skydeck at the Willis Tower. Perched on the 103rd floor, the observation deck boosts incredible 360 degree views of the city but the thick pieces of glass that create a ledge for you to peer down on the city at your feet is an exhilarating experience, especially for adrenaline junkies! I recommend going 1 hour before sunset as the light is best then.

360 Chicago Observation Deck

It’s really tough to choose which observation deck I like the best but the lake views and city views from the 94th floor of the John Hancock Building, at 360 Chicago are just stunning. the observation deck also features, TILT!, a tilting glass lookout 1000 ft. up

The Art Institute of Chicago

A classic and one of my favorites in Chicago, you’ll admire works by Claude Monet, Vincent van Gogh and more.

Photo op Tip: find this heavenly (and Instagrammable!) staircase in the modern wing.

Feel like you’re in New York City by exploring the West Loop

One of the reasons why I love Chicago so much is because it’s so neighborhoody which makes a big city feel more intimate. The West Loop / Greektown was the last place I lived before I moved to NYC in 2016 and I loved it because it reminded me of New York City a bit. If you ever visit Chi, I highly recommend making it out to the Weat Loop where you’ll find awesome views of the Willis Tower, cool SoHo-esque lofts and some of the best restaurants / coffee shops around (@girl.and.the.goat@auchevaldiner and my personal fav, Greek Isles, opa! just to name a few!

Where to Eat & Drink

The Hampton Social – Streeterville

The Hampton Social has seven locations in the US, inspired by East Coast vibes. We visited the Streeterville location in Chi and loved it! The restaurant has a beautiful outdoor patio on the second floor and the aesthetic are just as awesome as the dishes.

City Winery Riverwalk

The City Winery Riverwalk is one of my favorite places to have a drink and watch the boats go by. It’s an incredibly relaxing atmosphere and they have great bites too!

Bernie’s Chicago

Chicago is booming with tons of new restaurants to satisfy your taste buds. One of my favorite spots for lunch is Bernie’s Chicago. We indulged in everything from Pan con Tomate, Lamb Hashwi to Hanger Steak Salad and Croque Madame with their signature (and to die for I might add) Sangria to accompany this epic meal. Bernie’s is chef owned and operated by Chef Zack Sklar and Executive Chef Ryan Sand.

Where to Stay

Sonder Stay – Chicago

Life has really changed since March and I’ve been on lockdown in New York City ever since, so I decided that I needed a change of scenery and head to Chicago for a break from New York City. At first, I was hesitant to travel anywhere because I wasn’t sure if accommodations were ready to keep travelers safe, until I discovered Sonder Stays. Located in the South Loop of Chicago (they have many other locations in major cities around the world), my stay kept me feeling confidentially safe to enjoy my socially distant getaway. Everything was thoroughly cleaned and sanitized and the building and unit felt brand new! I loved my stay and will definitely opt for a Sonder Stay for my future, domestic short getaways this year. Check them out here!

  • Self check-in and contactless service, key fobs in unit to access the building
  • Professionally cleaned and disinfected
  • Stylish and cozy, comfortable design
  • A user friendly app to give you the scoop on your stay and provides you with a code to help you enter your unit
  • Text message service for any questions you may have you may have
  • Fully stocked kitchen (including coffee, pots, pans, cleaning products, etc) and bathrooms
  • In unit washer in dryer – huge plus

Virgin Hotels Chicago

The Virgin Hotels Chicago is one of my favorite hotels in Chicago because of its incredible vibes, perfect location steps away from the Chicago Riverwalk, its amazing views, awesome rooftop, Cerise, 26th floor and impeccably designed rooms. But I’m not surprised because anything by the Virgin brand always brings good vibes!

Langham Chicago

For architecture lovers out there, the Langham Chicago is set in a Mies van der Rohe landmark tower, surrounded by stunning views of the Chicago River and a glimpse of Lake Michigan.  

Due to the recent pandemic, Langham Chicago also kept my mind at ease with their Covid precautions. Everything from taking mandatory core body temps at the door, to sanitizing every inch of the place constantly, to hand sanitizer at every corner to electrostatic sprayed rooms and spaces and more. I appreciate how seriously they’re taking this and have been loving social distancing from here, surrounded by views of the Chicago river and Lake Michigan.

You may also want to consider booking the Langham’s Club Lounge which is open all day and offers breakfast, afternoon tea and evening cocktails and canapés. The lounge offers also offers sweeping views of the city, the river and the lake but my favorite feature? The gorgeous Writer’s Corner and Library. It’s safe to say I spent a ton of time here, relaxing while I worked.

The Hoxton Chicago

I used to live in the West Loop so when I heard there was a Hoxton opening up on the area, I immediately added it to my hotel bucket list. My recent stay was awesome. The lobby’s bar, coffee shop and restaurant are a hub for hip travelers and locals alike. The energy was amazing and I did not want to leave! The design is impeccable throughout every inch of this property and it’s totally Instagrammable. It’s also walking distance from some of the best restaurants the city has to offer such as Girl & The Goat, Au Cheval and more. This is the place to stay if you want to experience a hip local vibe as opposed to a touristy vibe.

All content provided on this blog is for informational purposes only. The owner of this blog makes no representations as to the accuracy or completeness of any information on this site or found by following any link on this site.

I was hosted by Choose Chicago and and the partners above. As always, all opinions are my own.



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  • Ray October 20, 2016 at 2:58 am

    You are so right about Chicago being such an under rated city. I’m from Toronto and I find that we have more in common with Chicago than we do with NYC on so many fronts – culture, people, scenery, craft brewery productions, arts & comedy, music, sports culture, etc. Best of luck to your new life in NYC.

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