Taking a vacation in Chicago is one of the best places for travel, with so many things to do during the summer and winter months, there is no chance of ever running out of fun things to do in Chicago for cheap. Chicago is by far one of my favorite vacation hot spots since my kids and grandkids live there, and since I used to live in the northwest suburbs of Chicago years ago, visiting my old stomping grounds will be a treat.
We’ve had a good time during our inexpensive Staycation vacations, but this year we decided we really needed a getaway vacation where we can fly to Chicago and enjoy the Windy City and its many attractions. Planning a cheap vacation trip to Chicago includes finding good deals on hotels, car rentals, air fare, discount event tickets and finding as many free activities as possible. When it comes to planning a vacation to Chicago or anywhere else, cheap is good, but free is better.
Deciding where to stay in Chicago, where to eat, where to park if you’re going to spend time in downtown Chicago or surrounding cities, and where all the hot spots are in or outside of the city are things that must be decided. Picking what hotels or motels we would consider for our visit to Chicago was easy with Hotels.com, and since I used to live there I know what neighborhoods are good or bad, and what areas to avoid at all cost.
Vacation to Chicago For Cheap
Chicago is well known for having many of the most popular restaurants, entertainment, shopping, transportation options, concerts and dance clubs, museums and year-round events that vacationers to Chicago can always find stuff to do for the whole family to enjoy. Even though my kids aren’t really “kids” anymore, we’ll still plan things to see and do that my grown children and the grandkids will enjoy that are either cheap or free, since we don’t want our vacation to Chicago to be a financial hardship for their budget as we run around town together.
Finding cheap round-trip airfare to Chicago and back wasn’t a problem at all because we had plenty of accumulated air miles on Mastercard that we used for our plane tickets, so flying to Chicago was basically free. We checked out local Chicago-area hotels online that were close to our final destination spot, searched for discounts and promotion codes, and managed to find a good quality, 4 star hotel at the right price and in a nice area.
I don’t know about you, but I don’t trust hotel ratings or “star” factors distinguishing a 5-star hotel from a 3 or 4-star hotel because anyone (including hotel owner relatives and friends) can post a good or bad rating to make the hotel/motel appear to be ranked better than it truly deserves. My husband looked at a few inexpensive hotels in and around Chicago and nearby suburbs on Google Maps with Street View and quickly realized we don’t want to stay at those hotels. Ever.
Tip: Make sure you don’t unknowingly choose to spend your vacation staying at a hotel that charges “by the hour”. Planning a vacation for cheap is one thing, but those kinds of hotels are not where we want to stay for a minute, let alone an hour or an entire vacation trip to Chicago or elsewhere.
Things to Do in Chicago
There are lots of fun things to do in Chicago that are dirt cheap or free, for families with kids, singles, married couples without kids etc. Here is a short list of 40 things to see or do in or around Chicago including Chicago Museums, with many attractions and events offering free days, coupons or deep discounts on admission.
- The Art Institute
- Field Museum of Natural History
- Museum of Science and Industry
- Museum of Contemporary Art Chicago
- Shedd Aquarium
- Adler Planetarium
- The Chicago Historical Society
- The Magnificent Mile
- “Sue” & the “Underground Adventure” at the Field Museum
- Chicago Cultural Center
- Garfield Park Observatory
- Ride bikes along Lake Shore Drive
- Chicago Children’s Theatre
- McCormick-Tribune Ice Rink
- Lincoln Park Zoo
- Brookfield Zoo
- Wrigley Field
- Navy Pier
- Grant Park
- Chicago’s Historic Water Tower
- Willis Tower Skydeck (formerly Sears Tower)
- Six Flags Great America
- Harpo Studios to see Oprah!
- Taste of Chicago
- Chicago Beaches
- John Hancock Building
- Planet Hollywood
- Civic Opera House
- Millennium Park
- Botanical Garden
- Butterfly Museum
- Buckingham Fountain
- Chicago Air & Water Show
- Chicago Blues Festival
- Frank Lloyd Wright Home and Studio
- Lambs Farm
- Medieval Times Dinner & Tournament
- Dave & Busters – Eat, Drink, Play
With so many things to do in Chicago and surrounding cities, two hot spots no one should miss out on is Chicago Style Deep Dish Pizza and Chicago style hot dogs. Chicago is famous for having the best hot dog and deep dish pizza, and those two things are on our “must do” list during our vacation to Chicago.
Chicago Vacation Packages
After checking out a number of vacation package deals for our Chicago getaway trip that includes the flight, hotel and rental car, we actually found the best deals for this vacation by simply going to each website individually. Discount codes and promotion codes advertised online were either bogus or already used when we started planning our vacation, so we won’t waste time looking for those anymore.
Vacations to Hawaii or similar getaways offering great package deals for all inclusive vacations, such as a resort vacations, might be well worth the extra effort trying to find those special package deals. The total cost of our vacation to Chicago including hotel stay, airfare, car rental and gas, money for food and entertainment etc is one of the cheapest vacations we’ve ever planned and not one penny of the whole trip to Chicago is being paid for with a credit card.
One very cool bonus with the Chicago-area hotel we chose through Hotels.com is that it has a kitchenette in the room besides other amenities like free internet access, to save money on eating out by fixing some meals in the hotel room kitchenette. I don’t know if I would call this vacation a “frugal” vacation or not, which would probably mean driving to Chicago instead of flying, but it sure has turned out to be a lot cheaper than we expected when we decided to take a getaway vacation to Chicago.