Chicago on a Budget; A Question and Answer

We receive a lot of questions about different places we go. We are always happy to help with any question that we can answer from our own experiences.  You may find our answers interestingly different, as nothing can take the place of experience. An overnight stay is not considered an experience as we define the word. We believe that time spent in any area is more than a one night stand to truly experience the area.

We will try addressing as many questions as our calendar permits. We are thinking of adding a new page or category  called questions and answers. It becomes a time management issue that we must resolve, but that’s our problem. You want answers and we do want to help.  Note, sometimes  we answer a question through our podcasts or twitter, @sfpworld.  Our  answer  based solely upon our own experiences, no bs. We even try direct e-mail answers too.  It is our intention to help based on what we have experienced and not on what others say or other websites. We want success on your holiday or vacation.

Feel free to contact us in any way possible, here at our contact us page or through twitter @sfpworld, Instagram at storiesfacesplaces, or our Facebook page.  We will be available for you as calendars permit.  In return, we ask you for your patience in receiving a response, and for your support for our podcasts and social media.  We seek reviews. Let us know what we can do to make it better for you and what subjects you would like us to gear our podcasts. We will in turn do our best for you. For now hang around and explore.


Given that, we recently received this question from our e-mail. Jack wished to remain anonymous and we respect that.

Q:  How do we, my wife and I do Chicago on a tight Budget?   We want to stay in a nice hotel downtown, but we don’t need fancy restaurants, fast food is what we will mostly be eating.  We would also like to visit some of the trendy neighborhoods, which ones?

A:  The hotel cost will be the largest part of your budget, given that the fancy restaurants are out of the question.  In your search for a hotel, you’ll be happy to know that Chicago sets itself up very well for putting in a “bid” price with sites such as Priceline, from which we receive no compensation.

A former Chicago resident, I often return many times a year, each requiring a hotel stay.  I prefer a top rated (4 star) hotel in the areas of the Magnificent Mile-River North or Millennium Park-Loop. Using the same system I have mentioned here, I often find one for around $100 per night.  As a back up, I sometimes  make a reservation at a hotel that has a free cancellation policy. Then I roll the dice on a bidding site. If I get a four star for a great price reduction, I then cancel  the back up.

Specifically and about a week before the trip I start placing bids for less than half the average price.   I make sure to specify only the previous mentioned areas and a four star or above. I find this strategy is one of the best ways to manage your overall costs.

As a note, these are the primo areas in Chicago and offer a walkable visit. In addition, the buses and “L” trains are easy to navigate and cost-effective.  Make sure to look for the free trolley that will take you to Navy Pier.

You mentioned fast food. I took that as typical Chicago “street food”.  Well,  there is no better city for inexpensive “street fare”.  Chicago’s great pizza, hot dogs,  and Italian beef sandwiches all make my mouth water just writing these words.  In addition, the many little local places, smattered throughout the city offer wonderful ethnic foods for very reasonable prices.  This is the Chicago I know, recommend, and should never be missed on any trip to the Windy City.

For some neighborhood experiences, make sure you take the blue line “L” train to Wicker Park/Buck Town, getting off at the Damen stop.  A walk around North Avenue and Milwaukee offers up great inexpensive food and unique shops.  To further your fun,  take the red line “L” train to Lincoln Park, get off at Fullerton, walk east toward the lake and walk Lincoln Ave. or Clark St. for shopping and restaurants.  Other stops on the red line will bring you to Lakeview or Boystown at Belmont or Addison. There you will find more unique neighborhood experiences with locally owned shops and restaurants.  These are just a couple of suggestions, as Chicago has many more wonderful neighborhoods with personalities all their own.  Wander and discover your own Chicago experiences!