Last Minute Flights from Chicago: Ideas for a Budget Getaway


The Windy City has an abundance of options for residents who want to take a last-minute vacation without breaking the bank. From cheap flights to nearby road-trip destinations, there are plenty of ways to take an affordable vacation. Whether you are looking to explore another city or camp out for an outdoor adventure, with a bit of flexibility and an eye for unexpected deals, travel deals from Chicago are quite achievable. In this article, we will explore some great options for spontaneous and budget-friendly travel from Chicago.

Last Minute Flights from Chicago

Last minute flight from Chicago departing

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Chicago is a great city for those looking to take a cheap vacation, as it is typically easy to find great deals on flights from Chicago. The trick to getting good flight deals is to be flexible with your dates, departures, and destinations. Can’t find a good price for flying out of O’Hare on a Friday night? Well, O’Hare is the most popular airport in Chicago, being that it is only 17 miles from downtown. Also, Friday night is one of the most popular times to travel, so that further increases demand. Try looking for a flight on a Thursday or in the morning, and try checking one of the other airports in the area. Chicago has two main airports, O’Hare (ORD) and Midway (MDW), and just over 80 miles away is Chicago Rockford Airport (RFD). 

If you can be flexible with your destination as well, that further increases your ability to find a good flight deal from Chicago. This can mean picking your destination just before your trip, or it could mean simply picking a different airport a little further from your intended destination. Being flexible with your flight destination gives you more options to shop around. Between flexible dates, checking different airports to depart from, and keeping your options open for destinations, you can often find better deals than if you just go with your first choice. 

Popular Flight Destinations from Chicago

A map of possible destinations for last minute flights from Chicago

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If you're looking for a budget-friendly vacation, consider taking a last-minute flight to Minneapolis. Minneapolis is a great city for a vacation - the downtown area is full of amazing restaurants, and the city is known for its art, music, and theater. It's also close to plenty of outdoor activities like boating, fishing, and camping. Plus, the cost of living is quite low compared to other major cities in the US, so you can stretch your dollar further when it comes to food, entertainment, and lodging.

Another great choice is a last-minute flight to New York City. While NYC isn’t exactly known for being affordable, there are plenty of free things to enjoy. Take a stroll through Central Park, visit the High Line, explore the Brooklyn Bridge, or take a free walking tour of the city. You can also take in some of the city's incredible street art and catch a free outdoor concert or movie. With so many free activities to choose from, a vacation in New York City can be one of the most affordable and enjoyable trips of your life!

Florida is another good option and there are plenty of options available to get you there. Once you arrive, you'll find plenty of affordable things to do, from relaxing on the beautiful beaches to people-watching on the city streets. The cities of Orlando, Tampa, and Miami are some of the most inexpensive places to stay in Florida, and each one has its own unique appeal. Although anywhere with a free beach to hang out at will do, and there is no shortage of those!

Milwaukee Road Trips

Milwaukee skyline

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You can also keep your vacation under budget by forgoing the airfare altogether and taking a short road trip. Just a two-hour drive north, Milwaukee offers plenty of affordable activities for travelers on a budget. Take a stroll through the historic Third Ward, where you can enjoy art galleries, unique boutiques, and farm-to-table restaurants. Check out the Milwaukee Public Market for a variety of delicious local eats, or take a tour of the Miller Brewing Company for a taste of the city's famous beer culture. With many affordable accommodations and free attractions like Lakefront Park and the Milwaukee Art Museum's stunning Calatrava-designed addition, Milwaukee is a great option for a wallet-friendly getaway.

Camping at a State Park

A waterfall at Starved Rock State Park

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Nearby state parks are another great option for a weekend road trip. Starved Rock, located just 90 minutes from Chicago, offers endless hiking trails, waterfalls, and stunning vistas of the Illinois River. With plenty of affordable lodging options nearby, from campgrounds to budget hotels, it's easy to keep the cost down. Or just under three hours northwest of Chicago, Apple River State Park is another great option for a cheap vacation. The park is known for its scenic hiking trails and the rushing Apple River, which is perfect for tubing or kayaking. Camping and cabin rentals are available at the park for lodging (although cabins cost similar to a hotel, so you may want to stick with camping). Whether you want a weekend of hiking and relaxation or a day of water activities, these two state parks offer plenty of affordable options for a cheap vacation close to Chicago.

Great Lakes Cruises

A cruise ship in Chicago

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Don't overlook the possibility of taking a cruise on the Great Lakes. Cruises departing from Chicago offer a range of affordable options, from budget-friendly three-day trips to weeklong itineraries with stops in destinations like Mackinac Island or Milwaukee. Many cruise lines offer last-minute deals and discounts to fill up remaining cabins, making it possible to score a great deal on a vacation by booking closer to departure. Onboard meals, entertainment, and accommodations are all included in the price, making it easy to stick to not overspend. Plus, the convenience of departing from Chicago means you won't have to spend extra money on flights or transportation to reach your departure point. So if you're looking for a cheap and spontaneous getaway, consider taking a cruise from Chicago for an affordable and enjoyable vacation.

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