$474 Cheap Flights to Chicago
One-way
Departing from
Santorini
Going to
Chicago, United States
Chicago (ORD)
United States • November, 2025
79% AI deal score
$1,325 $474
Chicago (ORD)
United States • November, 2025
76% AI deal score
$1,325 $479
Chicago (ORD)
United States • February, 2026
75% AI deal score
$1,325 $505
This is the lowest one-way flight price found by RatePunk users in the last 24 hours for a flight departing from Chicago. Fares are subject to change and may not be available for all dates. (Data last updated 11/11/2025).
Popular airlines to Chicago
American Airlines
Air Canada
Alaska Airlines, Inc.
JetBlue Airways
Delta Air Lines
Frontier Airlines
Spirit Airlines
United Airlines
317,956 searches in the past 7 days on RatePunk
Flight deals up to 90% off
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Top Cheap Flight Deals to Chicago
Recent round-trip flight deals to Chicago
Tue, Nov 18 - Mon, Nov 24
Cheapest
Santorini (JTR) - Chicago (ORD)
Aegean Airlines airlines • 2 stops • Athens (ATH), Istanbul (IST)
Chicago (ORD) - Santorini (JTR)
Turkish Airlines airlines • 2 stops • Istanbul (IST), Athens (ATH)
$1,325
$700
-$625
47%
Tue, Nov 18 - Thu, Nov 27
Santorini (JTR) - Chicago (ORD)
Aegean Airlines airlines • 2 stops • Athens (ATH), Istanbul (IST)
Chicago (ORD) - Santorini (JTR)
Turkish Airlines airlines • 2 stops • Istanbul (IST), Athens (ATH)
$1,325
$702
-$623
47%
Thu, Mar 5 - Tue, Mar 10
Santorini (JTR) - Chicago (ORD)
Aegean Airlines airlines • 2 stops • Athens (ATH), Istanbul (IST)
Chicago (ORD) - Santorini (JTR)
Turkish Airlines airlines • 2 stops • Istanbul (IST), Athens (ATH)
$820
$752
-$68
8%
Sun, Nov 23 - Thu, Nov 27
Santorini (JTR) - Chicago (ORD)
Aegean Airlines airlines • 2 stops • Athens (ATH), Istanbul (IST)
Chicago (ORD) - Santorini (JTR)
Turkish Airlines airlines • 2 stops • Istanbul (IST), Athens (ATH)
$1,325
$816
-$509
38%
Wed, Dec 24 - Wed, Dec 31
Santorini (JTR) - Chicago (ORD)
Aegean Airlines airlines • 2 stops • Athens (ATH), Warsaw (WAW)
Chicago (ORD) - Santorini (JTR)
LOT Polish Airlines airlines • 2 stops • Warsaw (WAW), Athens (ATH)
$1,325
$842
-$483
36%
Thu, Apr 16 - Sat, May 9
Santorini (JTR) - Chicago (ORD)
Big Sky Airlines airlines • 2 stops • Athens (ATH), Madrid (MAD)
Chicago (ORD) - Santorini (JTR)
Swiss International Air Lines airlines • 1 stop • Zürich (ZRH)
$820
$1,277
+$457
56%
The cheapest time to fly to Chicago
Ready to jet to Chicago on a budget? Check out these popular routes with surprisingly cheap fares (one-way prices):
Last-Minute Flights to Chicago
Need to get to Chicago ASAP? Even if you're booking a flight on short notice, there are often last-minute deals available:
Next 2 weeks deals
Last Minute Flight Deals!
Great deals have been found, with flights to Chicago departing in the next two weeks for as low as $816!
⌛ Last-Minute
Santorini - CHI
A great last-minute steal for a cross-country flight.
Found 2 days ago
$816
round-trip
Tip: If you don’t see your city listed, try a quick search anyway – new deals appear daily. Airlines sometimes slash prices a few days before departure to avoid empty seats.
Keep in mind, while last-minute fares can be lucky finds, booking about a month in advance generally yields cheaper flights on average. If you have flexibility, try to plan ahead. But if an unexpected trip to Chicago pops up, check our site – you might get lucky with a sudden fare drop.
Facts About Flights to Chicago
To help you plan your journey, here are some quick Chicago flight facts and tips.
Chicago city airports
Chicago is a major transportation hub with several airports serving the region. The two primary airports are O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). O'Hare, one of the busiest airports in the world, is located on the northwest side of Chicago and serves as a major hub for United Airlines and American Airlines, offering extensive domestic and international routes. Midway, located on the southwest side of the city, is a major base for Southwest Airlines and provides primarily domestic flights. A third option is Chicago Rockford International Airport (RFD), located about 85 miles northwest of Chicago. While farther away, RFD can be a convenient alternative, especially for travelers in northern Illinois or southern Wisconsin, and it's known for its cargo operations and passenger service from low-cost carriers.
O Hare International (ORD)
Chicago, United States
Chicago Midway International (MDW)
Chicago, United States
Chicago Rockford International (RFD)
Chicago, United States
Pro tip: search “Chicago (Any)” to see fares to all Chicago airports – sometimes one is cheaper than the others on your dates.
Insights for flights to Chicago
Cheapest airport
Chicago Midway (MDW)
Chicago Midway International Airport (MDW) is often the most budget-friendly option for your trip to the Windy City. Located closer to downtown than O'Hare, Midway offers a convenient and less chaotic experience, especially if you're looking to quickly dive into Chicago's famous deep-dish pizza scene.
Nonstop vs. 1-stop
100+ cities
As a major hub, Chicago acts as a connection point to over 100 cities with popular routes to both coasts, making cross-country travel a breeze.
Number of airlines
50+ airlines
Chicago is a major aviation hub served by over 50 airlines, so you'll have a plethora of options to choose from to reach your destination! Popular choices include full-service carriers like United and American Airlines, as well as budget-friendly options such as Southwest and Spirit.
Typical price range (round-trip)
Flights to Chicago: Unbeatable Deals Await! ($75 - $450)
Dreaming of deep-dish pizza and dazzling skyscrapers? Flights to Chicago typically range from $75 to $450, but prices can fluctuate. Keep an eye out for higher fares during summer and around the holidays, when everyone flocks to the Windy City. Consider flying during the shoulder seasons (spring or fall) for potentially better deals!
Flight frequency
2,000+ flights
Flights to Chicago are available daily, with increased frequency during the summer months and around major holidays. You'll find the most options during peak travel times!
ORD Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
ORD airport insights
Best days to catch a deal
Fri, Mon
Based on the provided data, Tuesday and Saturday are the best days to find flight deals from O'Hare International Airport. Tuesday has a count of 35 and Saturday has a count of 39, indicating these days had the most frequently observed cheapest deals.
Avg. deal survival time
11.3 hours
Deals from O'Hare International Airport typically last for around 11.3 hours. This short window means it's important to book quickly when you find a deal you like.
Rare deal frequency
16 deals
We discovered 16 rare flight deals for O'Hare International Airport in the last month. These rare deals earned an AI Deal Score of 90 or higher, often due to mistake fares, special promotions, or ultra-discounts.
Average price drop
-77%
On average, you can save significantly on flights from O'Hare International Airport, with prices dropping by an impressive 77.4%. This means you have a high chance of finding a great deal on your next flight departing from this airport.
Next 4 weeks: deal forecast
O'Hare International Airport Forecast
The forecast for O'Hare International Airport next month shows stable prices with a slight increase expected due to the holiday season. Travelers should book in advance to secure the best deals as prices are not expected to drop significantly.
Top 5 biggest price drops (last 3 months)
Found on November 7
Columbus - ORD
$2,825 → $126
96%
Found on November 9
Everett - ORD
$800 → $87
89%
Found on November 10
Liverpool - ORD
$3,400 → $443
87%
Found on November 7
Los Angeles - ORD
$720 → $108
85%
Found on November 6
Reynosa - ORD
$1,150 → $202
82%
Check these nearby airports too
Looking for more options? These airports near ORD sometimes drop rare deals too:
Gerald R. Ford International (GRR)
~13 rare deals/month
General Mitchell International (MKE)
~13 rare deals/month
Chicago Rockford International (RFD)
~6 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially GRR and MKE for long-haul deal surprises.
When Is the Best Time to Fly to Chicago
Timing is everything when hunting for cheap flights. Here are data-backed insights on the best times to fly to Chicago:
Cheapest month
January
Cheapest month
January is typically the cheapest month to fly to Chicago. The city is covered in snow, creating a beautiful winter wonderland. You can often find great deals on flights and hotels during this time, as it's after the holiday rush and before spring break season.
Best day to book
Tuesday
Best day to book
Tuesday is often the best day to book a flight to Chicago. Airlines tend to release new deals early in the week. Keep an eye out for flash sales and limited-time offers on Tuesdays to snag the best prices for your trip to the Windy City!
Cheapest days to fly
Wednesday
Cheapest days to fly
Flights on Wednesdays are often cheaper than on other days of the week. Mid-week travel tends to be less popular, leading to lower demand and better deals. Flying on a Wednesday can help you save some serious cash, leaving you more to spend on deep-dish pizza.
Advance booking sweet spot
2 months
Advance booking sweet spot
Booking about 2 months in advance is often the sweet spot for flights to Chicago. Airlines adjust prices based on demand as the travel date approaches. Booking a couple of months out can help you avoid last-minute price hikes and secure a better deal for your trip.
Seasonal considerations
Distinct
Seasonal considerations
Chicago experiences distinct seasonal changes, which significantly impact flight prices. Summer is peak season, with higher prices due to warmer weather and festivals. Winter sees lower prices, but be prepared for potential weather-related delays.
TL;DR: January is the cheapest month to fly to Chicago, offering a snowy cityscape and budget-friendly travel. Tuesdays are prime for booking flights due to airline deals, while flying on a Wednesday can save you money. Aim to book about 2 months in advance for the best prices. Keep in mind Chicago's distinct seasons, as summer is pricier and winter may bring weather-related disruptions.
Chicago Airports & Ground Transportation
One big question for travelers is which Chicago airport to fly into. Here’s a quick guide to Chicago’s airports and how to get to the city from each:
Chicago O'Hare International Airport (ORD)
O'Hare International Airport is one of the busiest airports in the world, serving as a major hub for United and American Airlines. With four terminals and numerous concourses, it offers a wide variety of dining, shopping, and lounge options to keep travelers comfortable. Located about 17 miles northwest of downtown Chicago, O'Hare is easily accessible via the 'L' train's Blue Line, offering a direct and affordable connection to the city center. The airport is known for its sometimes long walks between gates, so wear comfortable shoes! Don't be surprised to spot a plane taking off, it happens every minute!
Tip: Give yourself plenty of time to navigate this massive airport, especially if you have connecting flights.
Chicago Midway International Airport (MDW)
Midway International Airport, located on the southwest side of Chicago, is a convenient option for travelers seeking a closer alternative to O'Hare. It is a major hub for Southwest Airlines and provides a more streamlined and less overwhelming experience compared to its larger counterpart. The airport offers a selection of restaurants, shops and amenities. Getting downtown is a breeze, just hop on the 'L' train's Orange Line for a direct ride into the heart of the city. Perfect for a quick getaway!
Tip: Midway's smaller size means shorter walks, but it can get crowded, so arrive early.
Other airports
Okay, so Chicago is great, but sometimes the best flight deals land a bit outside the city! Airports like Milwaukee (MKE) and South Bend (SBN) can offer cheaper flights, but remember to factor in the commute to Chicago. Milwaukee is about 90 miles north, and South Bend is about 95 miles east, so plan for a bus, train or rideshare to get you to the Windy City.
Airport transfers
Getting around Chicago from its airports is a breeze with a variety of options! Public transportation via the 'L' train is super affordable, while taxis and rideshares offer door-to-door service at a higher price. For those who prefer to drive, rental cars are readily available, just be mindful of Chicago's traffic!
What to Do in Chicago
Chicago isn’t just about getting there – it’s about enjoying the country once you arrive! Here are some top things to do in Chicago, organized by interest:
Sightseeing & landmarks
Chicago is a city brimming with iconic landmarks! Make sure you visit Cloud Gate (aka "The Bean") in Millennium Park, ascend the Willis Tower for breathtaking views, and stroll along the scenic Riverwalk. Don't forget to check out the historic Water Tower and the beautiful architecture on display during a river cruise!
Arts & culture
Chicago's art scene is vibrant and diverse. Explore world-class institutions like the Art Institute of Chicago, catch a Broadway-quality show in the Theater District, and immerse yourself in the city's many colorful murals and public art installations. Be sure to check out a blues or jazz club for a taste of Chicago's musical heritage!
Food & nightlife
Get ready for a culinary adventure in Chicago! From deep-dish pizza to gourmet dining, the city offers something for every palate. Explore the diverse neighborhoods for authentic ethnic cuisine, and experience the lively nightlife scene, from trendy cocktail bars to blues clubs.
Shopping & fashion
Shop 'til you drop on the Magnificent Mile, Chicago's premier shopping destination! Discover high-end boutiques, department stores, and unique shops. Explore the trendy neighborhoods like Wicker Park and Bucktown for independent boutiques and vintage finds.
Nearby getaways
Escape the city for a day trip to one of Chicago's charming nearby destinations. Explore the beautiful beaches and dunes of Indiana Dunes National Park, visit the historic town of Galena, or head to Milwaukee to explore the breweries. These quick getaways offer a refreshing change of pace!
No matter your interest – be it art, food, nightlife, or nature – Chicago has something for everyone. And the best part? Many events and attractions refresh throughout the year, so there’s always something new to experience each visit.
Events in Chicago This Month
social mixer: cocktails & conversations @ the moxy
Join Windy City Social for an evening of mixing, mingling, and enjoying delicious cocktails with fellow young professional singles and new friends. Whether you're new in town or a seasoned Chicagoan, this is a great opportunity to expand your social circle and make new connections.
norman brown
Gametime offers last-minute concert tickets to see Norman Brown perform live at City Winery in Chicago, Illinois. Don't miss this chance to experience his smooth jazz stylings in an intimate setting.
smif-n-wessun
Find tickets to see Smif-N-Wessun perform live at City Winery Chicago on November 6, 2025, at 7:30 PM. Get ready for a night of classic hip-hop from these legendary artists.
glenn jones
Find tickets to see Glenn Jones perform live at City Winery Chicago on November 7, 2025, at 7:30 PM. Experience an evening of soulful music with this acclaimed R&B vocalist.
chicago symphony orchestra - muti & sainz villegas
Experience Rodrigo's captivating musical portrait of the royal palace and gardens near Madrid, featuring guitarist Pablo Sáinz-Villegas. His previous CSO performance was highly praised, and this promises to be another unforgettable concert.
Chicago Weather
Weather in Chicago
Mon, Nov 10
30%
2° -4°
30%
Tue, Nov 11
20%
5° -2°
20%
Wed, Nov 12
10%
9° 2°
10%
Thu, Nov 13
0%
11° 3°
0%
Fri, Nov 14
10%
14° 5°
10%
Sat, Nov 15
20%
17° 11°
20%
Sun, Nov 16
10%
14° 4°
10%
Here’s a quick look at the weather you can expect, plus this week’s forecast:
Seasons: Chicago experiences four distinct seasons. Spring (March-May) features gradually warming temperatures from 1°C to 16°C (34°F to 60°F) and blooming landscapes. Summer (June-August) brings warm temperatures ranging from 18°C to 29°C (65°F to 85°F) and sunny skies, but also humidity. Autumn (September-November) showcases colorful foliage and temperatures ranging from 21°C to 7°C (70°F to 45°F), with crisp air. Winter (December-February) is cold, with temperatures from -7°C to 2°C (20°F to 35°F), snow, and occasional blizzards.
Rain: Chicago experiences precipitation in the form of rain and snow throughout the year. Snow is more common during the colder months (November to March), while rain occurs frequently in spring, summer, and autumn. Precipitation can occasionally impact travel, especially during heavy snowstorms or periods of intense rainfall.
This week's forecast: This week in Chicago, the forecast shows a mix of weather conditions. Temperatures will range from -3.9°C to 17.4°C (24.98°F to 63.31999999999999°F), with mostly sunny, cloudy, and partly cloudy days. There's a chance of snow at the beginning of the week, transitioning to rain and possibly rain/snow mix later in the week.
(We update the weather forecast weekly so you know what to expect during your travel week. Always check a day or two before your flight for the most current conditions.)
Frequently Asked Questions About Flights to Chicago
(Have more questions?) Feel free to reach out or check our comprehensive Chicago travel guide. We’re here to help make your flight to Chicago (and the trip itself) as smooth as possible.
Pro Tips for Finding Cheap Flights to Chicago
Finally, to wrap up, here’s a cheat sheet of pro tips that experienced travelers use to save on Chicago flights:
Be Flexible With Your Dates: Sometimes flying on a Tuesday or Wednesday can save you serious dough compared to weekends. Play around with your dates to see the cheapest options – think of it as a fun game of travel Tetris!
Consider Alternative Airports: Chicago has two main airports: O'Hare (ORD) and Midway (MDW). Flying into one versus the other can drastically change the price, so compare both to snag the best deal.
Snatch Those Early Bird (or Late Night) Deals: Airlines often release deals at odd hours, so set those alarms or browse late at night. You might just find a fare so good, it feels like you're dreaming!
Embrace the Art of the Layover: Non-stop flights are nice, but flights with layovers are often cheaper. If you're not in a rush, embrace the layover and save some cash for deep-dish pizza!
Use Incognito Mode Like a Secret Agent: Airlines might track your searches and raise prices, so browse in incognito mode to keep them guessing. Think of it as your travel superpower!
Bundle Up! (Flights and Accommodation): Sometimes booking your flight and hotel together can unlock hidden discounts. It's like a travel combo meal – more for less!
Loyalty Programs: Your Ticket to Savings: Join airline loyalty programs to earn points and miles. These can lead to free flights, upgrades, and other perks. Start racking up those rewards!
Follow Airlines on Social Media: Airlines often announce flash sales and special deals on their social media channels. Stay in the loop to catch those fleeting offers!
Set Up Price Alerts with RatePunk: Let RatePunk do the work for you! Set up price alerts for your desired dates and destination, and RatePunk will notify you when the price drops. Never miss a deal again!
Consider Budget Airlines: Budget airlines can offer incredibly low fares, but be sure to factor in extra costs for baggage, seat selection, and snacks. Sometimes basic is brilliant!
By keeping these tips in mind, you’ll be well-equipped to find the cheapest flights to Chicago and make the most of your travel budget. After all, the more you save on your flight, the more you can spend on a Broadway show, a nice meal, or an extra tour in Chicago! 🎉✈️
