Are you looking for an ultimate baecation, girls weekend, family trip, or solo trip? Chicago is your answer. Here is a VERY full itinerary to an amazing weekend of my Top
Chicago “To Dos” to get a taste of what Chicago is all about. One of the largest and greatest cities in the world has so much to offer and I feel thankful that it is so easily accessible. Get ready to splurge, learn, eat, and enjoy yourself.
FRIDAY:
ARRIVE IN THE EARLY MORNING
-Morning: Stop over at Stans Donuts or Do-Rite Donuts and choose from a unique assortment after a long flight. Also find a Starbucks (one on every corner) and start the trip off with a strong coffee.
-Mid Morning: Head over to Navy Pier. Enjoy the new Ferris Wheel, updated facade, walk along the lake, grab a quick bite to eat while at Navy Pier. Enjoy great views of the city!
-Afternoon: Hop on the Afternoon Sea Dog Architectural Tour. Learn all about the city and appreciate its history and beauty. They sell cheaper tickets on Groupon!
-Evening: For the best ribs of your life hustle over to Twin Anchors. Rustic decor and very misleading, but very worth it!
-Night: Enjoy the one or a few of the many rooftop bars with incredible views. One we most recently came across is within The Conrad hotel and is perfect. This puts you in walkable or “Uberable” location to the River North area bars. Beware most bars in that area require a cover ($5-10) and have a dress code. Stout, Bub City, Three Dots and a Dash, Untitled, Pops Champagne, Headquarters, are a few random ones.
SATURDAY:
-Morning: Breakfast at The Grand Lux Cafe
-Mid Morning: Walkable is all the Magnificent Mile and its shopping glory. Go shop the day away along the strip or at Water Tower Place.
-Afternoon: After all that shopping you have to be hungry right? Stop at Chicago’s beloved Portillo’s and devour an Italian beef or Chicago Style Hotdog. If you are having a major splurge day get a chocolate cake shake!
-Evening: It will forever be The Sears tower to me, but for you The Willis tower.. go to the very top at night and get amazing views of the city! Buy your tickets ahead if time! It is a breathtaking view, step onto the Sky Deck and see the city from your feet thousands of feet below through only glass. Hope your not scared of heights!
-Night: Between numerous sports teams, concerts, comedians, shows, theater, etc! There is likely to be something you’d enjoy, treat yourself and go see amazing historical stadium like Wrigley, a performance at the beautiful Chicago Theater, Concert at the Jazzy House of Blues, or laugh out loud at a Comedy Show at Second City.
SUNDAY:
-Morning: Breakfast or Brunch at The Hampton Social
-Mid Morning: walk on over nearby and do a Chicago River Kayaking experience. Fun, educational, a tad stinky from the river but totally worth it for a unique view.
-Afternoon: You’ll see it on the kayak tour and will have worked up an appetite. Go stop at City Winery along the river for a few cocktails and delicious appetizers. You deserve it! OR If you are wanting some time away from the river walk area head over to The Purple Pig for a unique Mediterranean, tapas dining experience.
-Evening: For a splurge worthy Italian meal, head over to RPM Italian and enjoy some fine dining service.
-Night: Sample Chicago beers over at one of your favorites. Revolution Brewery, Goose Island, Half Acre, or Lagunitas! Take your pick.
Monday:
LEAVE LATER THAT NIGHT
-Early Morning: Get a quick bite to eat and coffee by your hotel and get on your walking shoes to beat the crowds. Walk through Millennium Park. Get your signature “Bean Photo” and check out all it has to offer around there.
-Mid Morning: Uber or walk to your favorite museum. With so many to chose from you could be here all week long. A few great ones are The Shedd, The Field Museum, The Science and Industry Museum, and Art Institute. Going on a Monday will help avoid some crowds.
-Early Evening: For a last hoorah to this eventful trip. Get yourself a fresh Giordano’s or Lou Malnati’s pizza. My personal favorite is Lou Malnati’s supreme pizza with all the goods. Then go have a food coma nap on your flight.
TIPS:
-Be SAFE. Don't walk alone, travel in bustling areas, Uber places..they are so cheap, and be aware of your surroundings. Its not that hard.
-Make dinner reservations in advance. Some even book up weeks in advance.
-Check out Groupon for Tour deals
-Stay at a VRBO or AirBnb to have better views and amenities, but hotels are never a bad bet!
-Buy everyone you love Garrets Popcorn. You can pick it up at the airport rather than try to squeeze it in your carry on.
-Chicago traffic is no joke. Id not suggest renting a car unless you are a Nascar driver.
-If you are crazy and do get a car, use Spot Hero to park. Use my promo code and get $10 any parking lot or garage you chose. Get their free App to make life easy.
-Look both ways before crossing.. Use the crosswalk signage, the taxi’s will not stop.
-Summer is known for every festival and concert you can think of, and winter you can enjoy the pretty Christmas decor and German market. Get to the airports early. At least two hours early. Although they are efficient, sometimes long lines cone out of nowhere and O'hare is massive. Better safe than sorry!
-Chicago has a horrible reputation currently, but bad things can happen anywhere in a small town or big city. Just trust your gut and stay out of questionable areas.
-Bring great walking shoes. You’ll do a ton of it and nothing is worse than a blister on day one.
-There will be lines in such a populated area. Don't be impatient like the rest of us Midwest people... You’ll get through it.
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