So, you’re planning a tour to the Windy City? From Millennium Park to deep-dish pizza to an awe-inspiring skyline, Chicago is a city that is a compulsory entry on every travel bucket list. However, before getting to the paradigm of wonders, the first challenge is the journey itself on an economy ticket.
So if you’re searching for cheap flights to Chicago, you’ve landed in the right zone. Well, if you plan a little, use the proper means, and are lucky with your timing, you should be able to snag some sweet deals on Chicago flight tickets and spend your well-earned dollars on things that matter-experiences, not airfare.
Best Tips for Cheap Flights to Chicago
1. Start with the Right Flight Search Tools
The absolute best way to begin searching for cheap flights to Chicago is by visiting the top flight comparison websites. Google Flights, skyscanner, Kayak, and Momondo are your best friends in comparing fares of different airlines.
- Google Flights lets you view fares across flexible dates and nearby airports.
- Skyscanner shows the cheapest months and even alerts you when prices drop.
- Momondo digs deep into fare trends and uncovers deals others miss.
These tools help you avoid overpaying and keep you on top of flash deals for cheap flights to Chicago today or in the future.
2. Be Flexible with Travel Dates and Times
Flexibility is the name of the game if you want to get really cheap flights to Chicago. The cheapest fares are usually on Tuesdays and Wednesdays, so try to fly midweek. Holidays really become an enemy at this time, as well as high travel times through summer or late December.
There are a few exceptions, of course; red-eyes and morning flights are often cheaper and less crowded, at least when considering direct service into Chicago.
3. Consider Both Major Airports
The Chicago metropolitan area has two international airports:
- O’Hare International Airport (ORD) – Some say it is the busiest airport in the U.S., which means plenty of domestic and international options available.
- Midway International Airport (MDW) – Less busy but usually cheaper, especially on budget airline flights to Chicago with southwest and frontier.
Search both when booking, and compare fares. Sometimes, flying into Midway can save you more than $100 on a Chicago flight ticket.
4. Book at the Right Time
With an emphasis: when to travel ranks highest in terms of importance, followed closely by when to book cheap flights. The sweet time for booking domestic flights is 1 to 3 months prior to departure. For international booking cheap flights to Chicago, the ideal time frame hovers around 2 to 6 months in advance.
The ultimate getaway, though, is less likely as many airlines announce flash sales on cheap flights to Chicago on such short notice, especially from the June to early September holiday. So, set up fare alerts!
5. Sign Up for Deal Alerts and Newsletters
Never underestimate the power of an email list. Sign up for alerts from:
- Scott’s Cheap Flights (Going.com)
- Airfarewatchdog
- Secret Flying
- Airline newsletters (like Southwest, United, and JetBlue)
These services often notify you of flash sales and mistake fares — perfect for grabbing cheap flights to Chicago if you’re flexible or spontaneous.
6. Use Airline Miles or Points
If you collect miles from a frequent flyer program or travel credit card, now is the time to redeem them. United and American Airlines both have hubs in Chicago, which makes redemptions a breeze.
If you do not have enough miles for a full award ticket, you may still be able to apply a few to reduce your total cost for any flight ticket to Chicago. In some programs, you are even able to “erase” the cost of travel purchases made after booking with points earned.
7. Go Budget with Low-Cost Airlines
Low-cost airlines save you bucks. Spirit, Frontier, and Southwest frequently advertise promotional fares and discounts for flights from Atlanta, New York, Dallas, etc., into Chicago. Of course, it’s a bargain, especially on direct cheap flights to chicago if you can give up on seat selection and snacks on board. Just make sure to have the price of bags or extras in mind.
8. Check Alternate Booking Strategies
Instead of booking round-trip tickets with one airline, You might find an affordable flight going to Chicago with one airline on a cheaper ticket while finding a cheaper airline for the return trip. Sites such as Kiwi.com and Hopper offer this option for flight combination, along with price-drop predictions.
Bonus tip: Use Skiplagged to explore hidden cities, whereby you book a layover in Chicago but do not take the second leg. Be careful with hidden city tickets, and do not check bags; airline printers do not take well to this trick!
9. Use a VPN and Incognito Mode
Airline prices fluctuate with your location and browsing behavior; you can reset your cookies, try your searches in incognito mode, or use a VPN to make it appear that you are searching for tickets from a different region.
Believe it or not, the same airplane ticket from Chicago is sometimes likely to be cheaper if bought in Canada or Europe. While this is not a guarantee for success, it is definitely worth trying.
10. Pack Light and Avoid Fees
Travel light to save maximum bucks. Excess baggage fees may take quite a bite out of your pocket. Most low-budget airline companies tend to charge for everything, including allocating extra hand baggage, checked baggage, and even the selection of a seat.
Restrict yourself to a personal item or a backpack that fits under your seat. Not only does this serve to keep your budget in check, but it will also ensure a smooth, quick process while walking through the airport, especially when catching last-minute cheap flights to Chicago today or transferring through a pretty congested hub.
Final Thoughts
For planning months ahead or to find today’s cheap flights to chicago a little flexibility and good tools can do wonders. With everything from using your VPN tricks to simply signing up for price alerts, every little thing brings you closer to booking cheap flights to Chicago.
Don’t wait for the fares to skyrocket. Use these proven strategies, compare the airlines, and stay tuned for promos. With the right timing and tools, you can bag the best flight ticket to Chicago available – and possibly save enough for that famous Chicago-style pizza.
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