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By Emmy Conway


Chicagoans don’t waste one second of summer. After months of dealing with chapped skin and icy roads, the locals shed their down coats and spring into public parks, street fests and that gorgeous lakefront trail. Head to Chicago for a memorable summer vacation. You’ll soon see that it ain’t no Second City.

Getting there:

Whether you arrive via plane or car, take the “L,” Chicago’s elevated train system to get around the city. Stations at both O’Hare and Midway airports make it cheap and easy to get into the Loop.  For a road trip, park at the city’s Park & Ride lots to avoid pricey downtown parking costs. A ride on the CTA L train costs $2.25 per person or $20 for a 3-day unlimited ride pass.

Where to stay:

Chicago Athletic Association

Chicago Athletic Association | Photo courtesy of Chicago Athletic Association

The best summer deals for Windy City hotels are in July and August. Stay near Millennium Park and the Art Institute of Chicago at hip new properties like the Chicago Athletic Association or the first of its kind Virgin Chicago which hosts all kinds of cool events in its public spaces.

Elsewhere around town, there are shabby chic budget options like the Freehand (which is helping to redefine the hostel concept) and the ACME Hotel Company as well as luxury options including the Langham Chicago and the Peninsula.

What to do:

Visit the Modern Wing at the Art Insitute of Chicago

Visit the Modern Wing at the Art Insitute of Chicago | Flickr CC: Patrick Morgan

Chicago offers a myriad of free things to do.  The lakefront includes 18 miles of open pathways, parks and beaches. One favorite stop is North Avenue Beach with its boat shaped bath house with a bar and live music on the top deck. There’s also the Lincoln Park Zoo, where admission is free year-round.

Another option is to join the locals and attend one of the many free summer festivals including Taste of Chicago (July 6-10) or the Chicago Air and Water show (August 20-21) among many others. Most cultural institutions also have free days designated throughout the year including the Art Institute of Chicago (every Thursday, 5-8pm), the Chicago History Museum (July 4, August 22-25 and August 29-31) and The Field Museum (August 11, 27 and 29).

Navy Pier, which is also free to walk around, has a fireworks show Wednesdays at 9:30pm  and Saturdays at 10:15pm through Labor Day weekend.

From one procrastinator to another, it’s never too late to book your summer trip to Chicago!

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Tagged: Family time, Midwest

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39 thoughts on “Wooed by the Windy City: Summer vacations in Chicago”

  1. My name is Tonya Blackshear a cancer survivor. I still have challenges but didn’t let that stop me at the age of 45 I went back to school for cosmetology & graduated with honors. Now I’m at Great Clips and working towards being sucessful & not letting cancer get the best of me. For years I wasn’t able to travel due to my illness but now that I have the permission from doctors, money is an issue. So a trip to Chicago or anywhere would do me good.


  3. I would love to visit Chicago and see my family that I’ve haven’t seen for over 30 years. I have heard that Chicago is a beautiful place to visit.

  4. I believe I love to visit all our beautiful cities here in the United States but of all the cities Chicago the famous skyscraper the Willis Tower the McCormick Place the taste of town Buckingham fountain the million dollar mile the famous state Street and so many places I would love to see Chicago would be my choice the big Windy City as Frank Sinatra say my favorite town Chicago is

  5. Hello my name is Shantaye I visited
    Chicago last year. I didn’t have a long visit. But I did see the lakeshore coming into Chicago it was beautiful. Please pick me I would love to have a longer visit and see the other beautiful sites Chicago has to offer.

  6. What a chance to visit family I haven’t seen in over 20 years!!!! What a surpise it would be for them….. there is no funeral!!!!

  7. To whom it may concern, im a home body, of course I’ve never been to Chicago, my dad says he took us to Disney Orlando don’t remember none of that since I iwas 5yr old. Oh well since then I’ve been NO Where. Please please please pick me.

  8. I would love an awesome amazing get away somewhere me and my boyfriend of ten years can go enjoy and experience something new that we both have never experienced…. We are both hard workers awesome parents and honest amazing friends

  9. Pick me! Pick me! I am a mother of six children and would love to have this opportunity to enjoy a great vacation without my babies!!

    1. Hi my name is Calvin Coble i would like to be pick 4 the Chicago getaway never been there . I can enjoy with my honey.

  10. Hi my name is martha. I would love to go to Chicago with my son. I hardly get out of New Jersey and this chance to win this trip will be a perfect mini vacation to explore Chicago please pick me

  11. I so very much need a get away……my significant other lives in Chicago im in Knoxville. And we never get to see each other.he works so very hard and very long hours. …Please help and allow ne this awsome get away…Thank you and god bless……

  12. I have not had a vacation in 25 years.With my children grown and families of there own and alone this sounds great,until I start reading other posts,more well deserving then I Good Luck to you all.

  13. Would love to visit the city I was born in. My parents moved away when I was one years old. And as being an artist it’s my dream to visit the Chicago Art Museum. I heard it is the”best” in the United States.

  14. I have a friend who is originally from Wisconsin. She has just saved to send her only child to her first semester of college. Then she will have no time after this fall for a vacation. She has raised her by herself with no help. It would be nice to take her back to one of her own favorite places.

  15. Hello!
    I am an educator of young kids. I want to visit the Field Museum in Chicago so I can “meet” Sue the T-rex and then I’ll tell my dinosaur-crazed students all about her in a great lesson!
    Seeing my favorite painting at the Art Institute would be really special, too. It is the “Sunday Afternoon…” work by Seurat. Another teachable moment is there, too, I suppose!
    Oh, and did I mention the Cubs and deep dish pizza? Zowee mama! as my students might say!
    Kathy in Jacksonville, FL

  16. I really really need this vacation, for me and my mom. She’s really a great lady and would really love to take her somewhere. ..she really deserves it! !

  17. There’s so many entries and I wish that we could just all go. Might as well jump in. Just a different scenery would make me drift away for a moment. I love being a single parent, but just a vacation from all the doctor’s appointments…MS and Fibromyalga are hell most of the time. Just a moment away…grateful!

  18. My husband and I take care of my disable sister and our 9 year old daughter, along with our whole family. We would so love a vacation right in the mid west not to far from home. In case something happens and we have to rush back.

  19. Recently I hooked up long distance with a childhood sweetheart. Being close to the retirement age we still haven’t been able to get together in person even though we plan to do so. Reading about all good things in Chicago and seeing you have an art museum which is perfect for him as he teaches art and college in Tennessee where he lives. Everything about the description of Chicago and all the things it has to offer is the perfect place for us to reunite.

  20. My Husband and I deserve to get away on a vacation. I have never been on a plane I have never left California I believe that Chicago is a beautiful city and he’s always been a dream of mine to go there and visit

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