Chicago for a Family of Four

The Deal Detective is SmarterTravel’s resident bargain hunter, Kate Hamman. She’s always on the lookout for new travel deals and invites you, dear reader, to submit your own questions.

amcnally writes, “We have the first week in August marked for our family vacation. We live in Ohio and would like our two boys (eight and 11) to fly for the first time this year. We are, of course, on a budget and are looking for a relaxing, not traditionally touristy destination to go for approximately five nights.”

I still remember the excitement of one of my first flying trips with my family. It was like boarding a spaceship, and my brother and I bickered for the window seat during almost the entire three-hour flight to San Diego. I applaud you for wanting to introduce your two boys to air travel, and I hope your flight is just as exciting, if a bit less turbulent.

When it comes to non-touristy destinations on a budget, several places jump to mind, including Chicago, San Diego, and Seattle. Though this list could potentially include places in Mexico, Canada, or the Bahamas, one of the best ways to cut down on costs is to stay local when traveling. That is, unless you come across a deal that’s just too good to pass up. Another thing to consider when traveling to less popular spots is that specials and discounts may be harder to find. Don’t fret, because there are a few ways to know you’re getting the most bang for your buck.{{{SmarterBuddy|align=left}}}For comparison’s sake, it’s best to price airfare to all three cities just to be sure you’re getting your money’s worth. For instance, I found round-trip flights from Columbus, Ohio, to Chicago in August starting at $219 per person, while round-trip airfare from Columbus to San Diego starts at $329 and Seattle starts at $332. Taxes and fees are included. Visiting Chicago versus the other two cities will save you $110 per person, or $440 for the family, which can make quite a bit of difference on tightened purse strings.

Now that you know Chicago will be the cheapest to fly to, you can turn your attention to finding a place to stay. Since Chicago is a large city filled with a range of accommodations such as hotels, B&Bs, and apartment rentals, you’re certain to find something that fits your bill. To begin, I priced hotel rooms for a family of four in August starting at $40 per night (without taxes and fees) at the Days Inn by the Chicago O’Hare airport. Hotels within the city start at about $71 per night (without taxes and fees), and many run closer to $150 per night. Be sure to read other traveler’s hotel reviews on our sister site, TripAdvisor, before booking. I’m going to guess that you would rather stay in the city center, meaning that a five-night stay would start at $355 (without taxes and fees). The total so far for a five-night trip to Chicago with air and hotel comes to $1,231 for your entire family (without taxes and fees).

Another option worth investigating, especially when traveling with a family, is renting an apartment during your stay. Vacation rentals are becoming an increasingly popular way to experience a city while traveling. They offer you the opportunity to live like a local and save on meals by cooking at home. Plus, many of them are more affordable than hotels, and offer a bit more space for a family than a cramped room. Apartments in the city start at about $100 per night (with taxes and fees), and most come equipped with a full kitchen. If you were to go this route, your total for a five-night stay with air and apartment comes to $1,376 (with taxes and fees), and can potentially cut the cost of food.

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The last thing to look for when planning a vacation is things to do, and Chicago is a veritable smorgasbord of activities. From the Field Museum’s largest T.Rex dinosaur ever found to the excitement and attractions of Nay Pier, you’re sure to find something that will satisfy all age groups.

If Chicago isn’t quite what you had in mind, you can still use the same general tools for booking a vacation. Just remember to compare, compare, compare. I hope your boys enjoy their very first flight, and that it leads to a lifetime of travel.

As for my other readers: Do you have a better destination for amcnally to take the family? Or do you have any recommendations on things to see or do in the Windy City?

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All prices, dates, and booking details listed here were valid at the time of publication. Some information may have changed since that time.