I’m heading to the windy city for Fourth of July weekend. John Mayer, whom I’ve always wanted to see live, is playing with the surviving members of The Grateful Dead at Wrigley Field on the first. I’ve also always wanted to visit Chicago, so instead of getting tickets to the concert in Los Angeles, I got tickets to the concert in Chicago!

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I wanted to share a couple of tips and tricks that I use when planning these kinds of trips. I’m still finalizing details, but first and foremost, a place to stay was pertinent. I used good ol’ booking.com, and after a few reservations and cancellations, because I found something in a better area or something cheaper, I settled on a decent spot a five-minute walk from Millennium Park.

RAKUTEN REVOLUTIONIZED THE WAY I SHOP ONLINE

I wanted something safe enough to walk to at night alone, convenient as far as attractions, comfortable enough to sleep, and affordable. Finding an affordable hotel in Chicago did not prove to be an easy feat. The hotel I opted for was a bit pricier than one I had previously booked and canceled but I decided the location was worth it and I would be getting cash back through Rakuten. If you do not know what Rakuten is, I suggest you sign up for it today. You, too, can begin receiving cashback for so many of your online purchases!

GETTING TO CHICAGO BY AIR

I’ve only ever been to Chicago’s airports, so stepping outside of O’Hare will be a long time coming. I booked my flight through Cheapair.com and I’ll be flying American Airlines to and from. I like CheapAir because they work with a company called Affirm that allows you to buy airfare today and pay later. Basically, like credit. I do not recommend this if you already have high debt or problems paying bills on time. It is convenient for those of us who may not have six hundred dollars to throw down on a flight to Tokyo today. We also know that that six hundred dollars is going to double in the next month, so we want to lock in that low price.

MY GO-TO RESOURCES FOR A PROPER WINDY CITY EXPERIENCE

As far as my itinerary, as I stated above, I’m still working out the finalizations. With that being said, I hit up Groupon and Goldstar for discounted tickets or events in the city I’ll be traveling to. I can conveniently filter my search by the dates that I’ll be traveling. Also, Rakuten is supported by Groupon, so anything bought through that website is currently seeing up to 8% cashback on purchases. Time Out Chicago is also a good resource for events and things to do and see. Their weekend editions are especially fantastic.

I recently stumbled upon Chicago Bucket List, a terrific Instagram account with over seven hundred posts on things to do, food to eat, and all-around fun in Chicago. What appealed to me the most about their account is that a lot of their posts are centered on less touristy locations coupled with gorgeous photos of a local’s life.

When I’m doing a Google search, I’ll usually type in something along the lines of, “off the beaten path (insert name of destination),” in the hopes that this return gets me visiting places that aren’t necessarily in every travel guide about the Midwest city. The more obscure, the more interested I am, though Shit Fountain, found in another of my favorite resources – Atlas Obscura, will have to wait for my second trip to Chicago. The pictures were enough.

CHICAGO DEEP-DISH DISDAIN

As a foodie, I’m very much looking forward to trying some Chicago cuisine even if it means deep-dish pizza. I shun the deep dish. Living in New York City for a couple of years, I simply became accustomed to my pie thin or all-around flat. I like to taste the toppings more than the dough, and I know I’ll get a lot of flack for that. Remember I said I’m going to try it. I’ve had deep-dish pizza before but I don’t need a Chicagoan to tell me I’ve never had deep-dish in the very place it was created. Also, if any Chicagoans out there are reading this and would like to suggest the place that I should try said deep-dish pizza, please don’t hesitate!

A while back, I made up a goal of spending July fourth and/or New Year’s Eve in a different location each year. I haven’t quite reached the consistency of this goal, but I’m on my way! What better city to celebrate Independence Day this year than Chicago? While our specific plans for that holiday are still pending, I don’t doubt it will be a memorable one. Twenty-seven days until departure! Until then, I hope you’ll sign up to receive the latest updates at The Road Linds Travels or visit my Facebook page and follow along there. Saluti!