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Get Blown Away by Windy City Deals

Not every Escape Under $500 I write about is feasible from every U.S. departure city, but I’ve found a destination that comes close. Hint: It’s a great place for deep-dish pizza, towering architecture, and “magnificent” shopping. And while it’s also known for baseball, its affordability has more to do with its “hubs” than its Cubs. Hopefully by now you’ve guessed Chicago, a city with one of the country’s busiest airports and a lot of good deals that follow.

Getting to Chicago

With the exception of Atlanta, Chicago’s O’Hare airport sees more passengers per year than any other U.S. airport. It also serves as United Airlines’ largest hub and American Airlines’ second-largest hub, which means competitive fares from departure points across the country. In fact, when I searched for August and September fares (including Labor Day weekend), I found flights departing from all four corners of the continental U.S. (Maine, Florida, Washington, and California), and just about everywhere in between, for less than $300. Here’s a sampling:

  • Detroit: $153 (American)
  • Miami: $176 (American)
  • Albuquerque: $198 (United)
  • Denver: $199 (United)
  • Raleigh: $205 (American)
  • Seattle: $207: (US Airways)
  • Wichita: $220 (United)
  • Rapid City: $233 (United)
  • Boston: $239 (American)
  • Dallas: $241 (United)
  • San Diego: $245 (US Airways)
  • Phoenix: $257 (American)
  • Portland, ME: $258 (United)
  • New York: $269 (United)
  • Los Angeles: $279 (American)
  • New Orleans: $285 (American)
  • Little Rock: $295 (American)
  • Billings: $296 (United)

Not surprisingly, major cities like New York and Los Angeles are clearly represented; however, I was pleased to find equally good—if not better—fares from smaller cities like Wichita and Portland, Maine. If you don’t see your city on my list, do a search on your own, and you’ll likely find reasonably priced results. Also compare fares to Midway, Chicago’s secondary airport, which is served by low-cost carriers like AirTran and Southwest.

Staying in Chicago

Because Chicago is such a big city, you can find hotels in any price range and style, and there always seems to be something on sale. If you want to stay at an affordable and trendy property that’s set in the thick of things, the Avenue Hotel Chicago, opened this spring and located about a half block from The Magnificent Mile, is priced just right. The hotel offers 20 percent off its “Best Available Rate,” and when I looked, I found rooms for $144 per night in August. With taxes, a two-night total came to $332.35, or $166.18 per person if you share a room. The hotel also offers a slew of themed packages such as “Techno Geek,” “Stay for the Cure,” and “Kids are Cool.”

For more deals on Chicago hotels, look to the major online travel agencies, which post Chicago discounts on a continual basis. For example, Expedia is currently running a 40-percent-off special for the Avenue Hotel through September 30, as well as discounts on 17 other hotels. In its Big City Sale, Orbitz lists various hotel discounts such as 20 to 30 percent off multiple-night stays at the four-star Hotel Allegro, which has discounted rates from $151 per night. Spotlighted on Quikbook is a handful of deals, including rates from $126 at the Congress Plaza Hotel through the end of September, while is offering properties with rates under $150, although many are located outside the city center.

If you want to get away for Labor Day, or any other quick weekend, try, which almost always posts Chicago travel packages. When I checked, August air-and-hotel getaways started at $259 per person, including taxes and fees, from Denver, and $269 per person from Boston. Of course, many other cities are available at similar prices.

Cost Breakdown

Here’s the cost breakdown for the most expensive airfare on my list paired with hotel, based on two people traveling together:

$296 (airfare from Billings) + $166.18 (two nights at Avenue Hotel Chicago) = $462.18 per person

Depending on your departure city and hotel of choice, you might be able to stay a third night and still keep within the $500 budget.

Taking Advantage of Chicago Discounts on Attractions

At the end of July, Smart Destinations launched its new Chicago Explorer Pass, claiming to save up to 35 percent on area attractions such as the Art Institute of Chicago and The Hancock Observatory. Since the card stays active for 30 days, it’s a great option for extended stays. If you plan to visit many attractions, be sure to compare the Explorer pass with the Go Chicago Card or CityPass to make sure you’re getting the right pass for you.

Been to Chicago or know of a great deal? Comment below on your favorite money-saving tips, activities, or places to eat and stay. Or, post questions for fellow travelers to answer.

(Editor’s Note: is a member of the TripAdvisor Media Network, an operating company of Expedia, Inc. Expedia, Inc. also owns and

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