Planning Your Chicago Staycation; Exploring Chicago for the First (thousandth) Time


Yay! Spring is here and Summer is just around the corner! It's time to start planning your summer- are you going on a cruise? Are you going to travel across the country or bike through Europe? How about a trip to Hawaii, or Italy, or Austria?
If you are, I'll admit I'm jealous. I wish I were small enough to stow away in your luggage- although that might not be legal, comfortable, or ideal for either of us. :) BUT because I'm not small enough, I've decided to stop moping and instead check out my Stay-Cation options here in Chicago. To my delight and surprise, I've realized that there's no real reason to leave Chicago for anything! Everything we're looking for in a great vacation is just a couple stops down on the 'El'!


What do you look for in a great vacation location? Here's a few of mine:

1. Great sun. At first I thought that sun-bathing in the city was only for tourists, old men in speedos and cute chicas in tiny bikinis. But I'm wrong. There are great places to be out in the sun AND be classy, chic, and Chicagoan at the same time. Montrose Beach (Brown Line, Montrose stop OR Red Line, Wilson stop) is a gorgeous beach a little out of the way of the usual, tourist-and-college-kid crowd. I'm only 21, but even I don't want to go to those overcrowded weekend beaches where you can't hear yourself think and your rays are blocked by some 6ft tall frisbee player kicking sand in your face. Ugh.

Another way to get great sun during your Chicago staycation is walking. Get outside and walk through one of the city's 500+ parks! The Chicago Park District does a great job at maintaining its parks so that people like us can walk through them and enjoy the peaceful sunny joy that walking through a summer garden brings us. Lincoln Park (Brown Line, Armitage stop), Jackson Park (Green Line, Ashland/63rd stop), Montrose Park (Red Line, Wilson stop), Humbolt Park (Blue Line- O'Hare Branch, California stop), even Garfield Park (Green Line, Conservatory/Central Park Dr stop) are beautiful parks that are open every day to walk through and enjoy. Lincoln Park also has the free Lincoln Park Zoo to enjoy!

Want to find more places to catch some great rays? Scroll down and click on the CTA Line you live off of.


2. Awesome shopping. We all know there's more shopping in Chicago than State street and the Magnificent Mile, right? Check out Wicker Park (Blue Line, Damen stop), where you can find knock out styles at knock out prices. Crossroads is a vintage resale shop where I bought my lace, vintage wedding dress for $14 dollars! Across the street is Myopic Bookstore, the BEST place to walk around and read books on a rainy day. The three-floor shop is piled high with books, all types, shapes and sizes! Reckless Records is a trendy record store with oodles and oodles of records, CDs, cassettes, and DVDs. The cute boutiques, shops, restaurants and cafes in this area takes more than a day to explore.

After you check out there, run over to Lincoln Square (Brown Line, Western), where you can find farmers markets, and enough shopping and exploring to fill in another whole day of staycation!

Love to shop? Well I have more places! Scroll down and click on the CTA Line you live off of.


3. Relaxation. I agree with all of you when you say that finding a quiet, relaxing place in the middle of the city is hard to do. That's why I decided to go out and find the most relaxing places in Chicago- and of course, they have to be free! First place I found was just down the street from my house, and completely free everyday- the Garfield Park Conservatory (Green Line, Conservatory/Central Park Dr stop)! Filled with plants and trees and exotic flowers, this is one of the most inspiring, relaxing, beautiful places I've ever seen! I go in with a book or my journal and sit on the bench next to the pond in the Aroid house or in between the cacti in the Desert house and just breathe.

Another place is the Jay Pritzker Pavilion (Loop, Madison/Wabash stop). On a gorgeous, sun-filled day or a clear, star-studded night, laying out on the grass and being surrounded by the music of the Grant Park Symphony Orchestra is the best place in the world. Especially on days when there are few people and you are free to roam the gardens and sit on the benches without too many kids or couples interrupting the moment.

If music and plantlife aren't your thing, check out St Michael's Parish (Brown Line, Sedgwick), one of the oldest historic cathedrals in Chicago. The intricate paintings and carvings, and the magnificent architecture just takes your breath away when you enter. Slide into a pew and gaze at the details of the paintings and sculptures that decorate the walls and ceilings, write or read, or just think. St. Peters in downtown (Loop, Washington/Wells), or St. Mary of the Angels (Brown Line, Armitage) are both cathedrals that have deep history and beautiful architecture, each unique in it's artistic look and feel. On my free day, I love to Cathedral hop- riding the 'El' from one cathedral to the next, reading a book and taking in the sights, sounds, and inspiration as I go.

Relaxing is great- especially if you don't have to go far, like me! For places near you, scroll down and choose which CTA Line you live off of.


4. Interesting Sightseeing. Is there anything "touristy" you haven't done in Chicago yet? Sometimes its the tourists that have all the good connections to Chicago. Pick up a tourist guide at a hotel or attraction and take a peek at what everyone else is coming here to look at. Take advantage of your city's attractions! Have you ever walked out into the glass box of the Sear's Tower Skydeck? Have you taken the Architectural Tour Cruise? Walked through Navy Pier and watched the fireworks? Even though we Chicagoans will never admit it, sometimes the guide books know Chicago better than we do.

If you've done all of those things and are ready for a challenge, more great places in Chicago for sightseeing are its ethnic and cultural neighborhoods. Pilsen and Little Village are Mexican neighborhoods full of Mexican food, culture, and fun. The National Museum of Mexican Art (Pink Line, 18th st stop) is a free museum in this area! Little India (#94B North Western bus, Western and Devon stop) has great middle-eastern food and groceries that are exotic and exciting! You can browse through the shops that carry authentic Indian and Hindu clothing and books, and explore the open markets. Chinatown is full of sights and smells that are true to Chinese culture- the architecture and decor vibrant and colorful, and the markets bustling and aromatic. Using your knowledge of the CTA and the city to your advantage, you can make your Staycation Sightseeing exciting and new every day.

You can Staycation Sightsee everywhere! Check out more places below, just choose which CTA Line you want to explore!


5. Sexy Nightlife. We all know why we go on vacations- the sex is so much better than at home! But I promise you that you can spice up your love AND night life during your Chicago staycation. With a little innovative thinking and an adventurous spirit, you can enjoy everything Chicago has to offer, day or night. Go wine tasting at The Poison Cup (Brown Line, Armitage stop), or check out a night party and live music at The Tonic Room (Red/Brown/Purple Line, Fullerton stop).  Take a evening walk along the shore, and watch the Navy Pier fireworks over the water. Do something that you never do (climbing a roof to see the skyline, or walking over the bridge on Lower Wacker to see the city lights reflect off of the River), and do it with that special someone.


More places, just choose what CTA Line you live off of:









Well, those are just a few of mine- but let me know what YOU look for in a great Staycation and I'll put it in a post!


Leave a comment
  • Chicago has 77 neighborhoods - not parks. There are over 500 parks in Chicago. Thanks.

  • In reply to bd95:

    Oh dear, thanks so much! I got the numbers mixed up! Thanks again, Ill change it right away

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