$432 Cheap Flights to Chicago
One-way
Departing from
Florence
Going to
Chicago, United States
Chicago (ORD)
United States • February, 2026
84% AI deal score
$1,030 $432
Chicago (ORD)
United States • February, 2026
84% AI deal score
$1,030 $434
Chicago (ORD)
United States • February, 2026
84% AI deal score
$1,030 $433
Top Cheap Flight Deals to Chicago
Recent round-trip flight deals to Chicago
Thu, Dec 4 - Wed, Dec 10
Cheapest
Florence (FLR) - Chicago (ORD)
TAP Portugal airlines • 1 stop • Lisbon (LIS)
Chicago (ORD) - Florence (FLR)
TAP Portugal airlines • 1 stop • Lisbon (LIS)
$1,030
$510
-$520
50%
Thu, Dec 4 - Sun, Dec 7
Florence (FLR) - Chicago (ORD)
TAP Portugal airlines • 1 stop • Lisbon (LIS)
Chicago (ORD) - Florence (FLR)
TAP Portugal airlines • 1 stop • Lisbon (LIS)
$1,030
$510
-$520
50%
Thu, Dec 4 - Mon, Dec 8
Florence (FLR) - Chicago (ORD)
Lufthansa airlines • 1 stop • Munich (MUC)
Chicago (ORD) - Florence (FLR)
Lufthansa airlines • 1 stop • Munich (MUC)
$1,030
$669
-$361
35%
Mon, Feb 2 - Mon, Feb 16
Florence (FLR) - Chicago (ORD)
Swiss International Air Lines airlines • 1 stop • Zürich (ZRH)
Chicago (ORD) - Florence (FLR)
Swiss International Air Lines airlines • 1 stop • Zürich (ZRH)
$1,030
$695
-$335
33%
Wed, Mar 4 - Fri, Mar 20
Florence (FLR) - Chicago (ORD)
Formosa Airlines airlines • 1 stop • Madrid (MAD)
Chicago (ORD) - Florence (FLR)
SAS Braathens airlines • 1 stop • Copenhagen (CPH)
$730
$849
+$119
16%
Thu, Feb 19 - Sun, Mar 1
Florence (FLR) - Chicago (ORD)
Formosa Airlines airlines • 1 stop • Madrid (MAD)
Chicago (ORD) - Florence (FLR)
TAP Portugal airlines • 1 stop • Lisbon (LIS)
$1,030
$1,002
-$28
3%
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
Find flights to Chicago starting from $416, departing in the next two weeks.
⌛ Last-Minute
Florence - CHI
A great last-minute steal for a cross-country flight.
Found 1 week ago
$662
one-way
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
ORD Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
ORD airport insights
Best days to catch a deal
Thur, Tue
Based on the provided data, Saturday is the best day to find cheap flight deals from O'Hare International Airport. Wednesday and Sunday also appear to have a higher chance of deals compared to other days.
Avg. deal survival time
14.4 hours
Deals from O'Hare International Airport last 14.4 hours on average. This means you have less than a day to book a flight you find.
Rare deal frequency
9 deals
In the past month, we've identified 9 rare deals for flights to O'Hare International Airport. These rare deals earned an AI Deal Score of 90 or higher and typically include mistake fares, special promotions, or ultra-discounts.
Average price drop
-78%
On average, prices drop by 78.3% from the peak price to the lowest for flights departing from O'Hare International Airport. This could mean significant savings if you're flexible and monitor prices for flights from this airport.
Next 4 weeks: deal forecast
O'Hare International (ORD) Flight Forecast - Next Month
Based on current trends, flight prices to O'Hare International are expected to remain relatively stable over the next month, with a slight increase expected around the Thanksgiving holiday. Travelers looking for deals should consider booking flights departing and returning on less popular travel days.
Top 5 biggest price drops (last 3 months)
Found on November 10
Columbus - ORD
$2,825 → $116
96%
Found on November 9
New York - ORD
$773 → $93
88%
Found on November 11
Everett - ORD
$800 → $97
88%
Found on November 11
Bellingham - ORD
$775 → $93
88%
Found on November 10
Liverpool - ORD
$3,400 → $443
87%
Check these nearby airports too
Looking for more options? These airports near ORD sometimes drop rare deals too:
Gerald R. Ford International (GRR)
~14 rare deals/month
General Mitchell International (MKE)
~5 rare deals/month
Chicago Rockford International (RFD)
~4 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.
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!
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!
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 Weather
Weather in Chicago
Wed, Nov 12
10%
13° 3°
10%
Thu, Nov 13
Frequently Asked Questions About Flights to Chicago
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.
