Cheap Chicago Vacation Ideas

Cheap Chicago Vacation Ideas

Trouble finding cheap vacation ideas? If National Lampoon has taught us anything, it's that vacations can be a little stressful. A lot of the time you're so busy trying to plan the odds and ends of what is supposed to be your escape from it all that you forget to relax. And in this Fiscal Cliff diving time of ours I'm pretty sure the inside out pocket is about to be a budding fashion trend. But don't fear, I, Shavon Coleman, on behalf of 4-Star Explorer will help you plan a stress free, roadworthy trip that even the Griswolds would envy.

The term staycation, cousin to the vacation, has only been around for a decade and spawns images of backyard inflatable swimming pools and cheesy tiki themed decorations. What originated as a way to deal with a slowly declining economic market as well as enjoy short periods of time off, the staycation is quickly getting refined as the chicest of mainstay outings. And instead of charting off to an unknown area and spending next to your life savings just to eat and get around, why not head a stone's throw to the nearest big city and spend pennies on the dollar instead? Not to mention a safety net of friends and relatives in case you run into trouble. So how do you begin this tremendous excursion? As with bank heists and football offenses alike, you've got to have a plan to get the score.


Planning is undoubtedly the most stressful part of the staycation. There are tons of travel sites out there to choose from, all claiming to have the best deals. This process often times hinders would be travelers from ever getting their trip off the ground. Many can not deal with sifting through tons of information as well as unforeseen extra prices. I found two websites that have become my go-to when traveling and offer the best prices with little fuss.

Lured in by the funny commercials, one day I decided to test just how well their travel services worked. I loved the easy interface of the site as well as being able to choose up to 5 other popular travel sites. The site automatically brings up separate windows for each site so that you can explore them individually or search through the Kayak main screen to see price breakdowns for a particular hotel in your area.


You know the jingle by the heart. And the added fact that they've brought the reemergence of the acting prowess of William Shatner. And because they offer no frills savings for those trying to land a descent hotel room. What makes Priceline a better choice than other sites is the "Pay When You Stay" icon. This waives the website's fees and lets you pay majority of the hotel bill once you arrive, all on the basis that you pay for at least one night of your stay. If you are staying for two or more days it would obviously behoove you to take advantage of this option. You'll also enjoy the "Name Your Own Price" tool. But be warned, you can save a bundle with this option but you won't know what hotel you are actually staying in until the bid is accepted. They will, however, give you a list of hotels in that area they have a partnership with.

Other Planning Issues

-If some R&R in the city is what you need, the second biggest thing to stress over will most likely be parking. And I'm not sure if you've heard the word but parking is at an all time high in Chicago. That added to the overnight towing law that passed this past December, you'll best make it leaving the sedan at home. Instead, pop over to your nearest Walgreens and buy yourself a Fun Day CTA bus pass that will allow you to ride the rails and buses for a 24-hour period.

-Download Google Maps! This handy guide helped me survive majority of this trip. In loo of printing out directions and bus schedules, Google Maps allows you to enter where you need to go from your current location and gives you the best method of transportation to get to your destination. They also have a handy step by step walking option that acts as a walking GPS. Depending on how your service is in some of the more industrial areas, the GPS may act a little fuzzy so don't be afraid to look a little awkward trying to line yourself up with the little blue arrow.

-Alert loved ones to your plans. It might feel a little weird "checking in" but that's what your safety net is for. Let them know where you are staying and where you plan to go just in case you lose your belonging or get lost.

The Getaway

It can be tough to make the city you see frequently into something shiny and new but adding some key elements can make you feel like a tourist any day. With a city like Chicago and it's varying neighborhoods, there's most likely a side you haven't seen. Try to stick to the formula of CFE, Culture-Food-Entertainment. Try any of the numerous museums or fall in love with the stage in the Theater District or just spend your time amongst the stacks in one of the many grand Chicago libraries. Splurge on fine least finer dining than your usual TGI-What'sIt. is an excellent resource for finding an exceptional restaurant within your price range. Lastly, what entertains you? The Blue Man Group is anything but usual and will only set you back 50 bucks and the view is just as nice from the balcony. (Not to mention you won't have to worry about being forced to volunteer on stage.) The whole point of taking a staycation is to strike out and see something not only new but more edgy than usual. Here's a run through of where we ventured out during our metropolitan retreat.

Holiday Inn Express-Magnificent Mile-$69 per night

What was formally Hotel Cass, is now remodeled into a swank new hotel with retro vibes. The rooms are a bit compact but if you happen to be riding solo or in a couple it's the perfect size. The standard amenities are revamped with 32 inch flat-screen TV, iHome alarm clock, room safe, fresh towels and all of the other creature comforts right down to the little soaps and shampoos. They also have a business center near the main lobby with computers and internet access but I discovered this wonderful little machine that popped out perfect pancakes all assembly line style and rolled out in two minutes. Truly a wonderful human achievement.

Chicago Cultural Center-free

Enjoy some of the greatest relics of or relating to Chicago while exploring 6 floors of masterful architecture, photography, and exhibits. CCC is one of oldest standing history venues as well as one of the latest to stay open and always free. You can kill hours getting lost in these adorned discoveries.


Nestled on the corner of Wacker and Randolph is what I deem as fine dining for the frugal. Don't want to leave a security deposit just to eat a meal? Tired of not being able to pronounce anything on the menu? Primbar offers a charmingly rich setting from the hard wood paneling to the leather lined booths to the signature fine wines and beers. And you'll love the crumbly topping of their stylish but hearty macaroni and cheese, you will actually want to marry it. (I had to divorce it though, it was coming between my love triangle with chocolate and fine spirits.)

Bob San Karaoke-$4-$9 per drink

Have you ever wanted to be on American Idol without the crippling embarrassment or without having to witness the diva antics of Sticki Minaj and the Incorrigible Mi-Mi? I've found you a gem of an outing for all you Karaoke Heroes. Cheers might be where everybody knows your name but here, everybody knows your song and will cheer you on even during your personal rendition of Don't Stop Believing. In addition, a full night of indoor caroling will cost you nothing but a beer or at least one drink to get the party going. And I could write a whole article on the bar tending entity known as Dave Lemiux. When you step into the place make an A, B, and C line to the bar and pray that Dave is making your drink.

In review, staycations are making a strong comeback especially during this New Year buzz. If you've got a few days and  a few dollars to spare make the time to refresh and renew.

For more pictures from our Staycation and exploration around the city, check out our facebook page at and don't forget to hit the "like" button! Have somewhere for us to venture out next? Email us at

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