$199 Cheap Flights from Tucson International to Chicago
One-way
Departing from
Tucson International
Going to
Chicago, United States
Chicago (ORD)
United States • May, 2026
86% AI deal score
$785 $397
Chicago (ORD)
United States • August, 2026
81% AI deal score
$770 $397
Chicago (ORD)
United States • April, 2026
79% AI deal score
$393 $199
Chicago (ORD)
United States • April, 2026
78% AI deal score
$393 $204
Top Cheap Flight Deals from Tucson International to Chicago
Recent round-trip flight deals to Chicago
Wed, Apr 29 - Wed, May 6
Cheapest
Tucson (TUS) - Chicago (ORD)
United Airlines airlines • Direct
Chicago (ORD) - Tucson (TUS)
United Airlines airlines • Direct
$393
$345
-$48
12%
Wed, Apr 29 - Wed, May 6
Tucson (TUS) - Chicago (ORD)
United Airlines airlines • Direct
Chicago (ORD) - Tucson (TUS)
United Airlines airlines • Direct
$393
$345
-$48
12%
Tue, May 19 - Tue, May 26
Tucson (TUS) - Chicago (ORD)
United Airlines airlines • Direct
Chicago (ORD) - Tucson (TUS)
United Airlines airlines • Direct
$393
$345
-$48
12%
Wed, Apr 29 - Wed, May 6
Tucson (TUS) - Chicago (ORD)
United Airlines airlines • Direct
Chicago (ORD) - Tucson (TUS)
United Airlines airlines • Direct
$393
$345
-$48
12%
Wed, Jun 3 - Wed, Jun 10
Tucson (TUS) - Chicago (ORD)
United Airlines airlines • Direct
Chicago (ORD) - Tucson (TUS)
United Airlines airlines • Direct
$385
$345
-$40
10%
Wed, Apr 29 - Wed, May 6
Tucson (TUS) - Chicago (ORD)
United Airlines airlines • Direct
Chicago (ORD) - Tucson (TUS)
United Airlines airlines • Direct
$393
$345
-$48
12%
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 from Tucson International 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!
We found last minute flights to Chicago departing in the next two weeks, with prices starting from $259.
⌛ Last-Minute
Tucson - CHI
A great last-minute steal for a cross-country flight.
Found today
$311
one-way
Facts About Flights from Tucson International 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.
ORD Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
ORD airport insights
Best days to catch a deal
Wed, Tue
Based on the data, Saturday has the highest chance of finding the cheapest deal at O'Hare International Airport. Sunday is also a good day to look for deals, as it has the second-highest count.
Avg. deal survival time
16.4 hours
Deals from O'Hare International Airport typically last around 16.4 hours. This means you'll want to book quickly if you see a flight you like from O'Hare!
Rare deal frequency
14 deals
We've discovered 14 rare flight deals for O'Hare International Airport in the last month. These deals, identified by an AI Deal Score of 90+, typically include mistake fares, special promotions, or ultra-discounts.
Average price drop
-70%
The average price drop for flights to O'Hare International Airport is a substantial 70.2%, indicating significant potential savings for travelers. This considerable decrease suggests that waiting for price reductions could lead to more affordable travel options when flying into this airport.
Next 4 weeks: deal forecast
O'Hare International Airport Next Month Forecast
Based on current data, flight prices to O'Hare International Airport are expected to remain stable next month. There are no significant price drops or increases anticipated in the forecast.
Top 5 biggest price drops (last 3 months)
Found on April 1
Columbus - ORD
$2,825 → $149
95%
Found on March 27
Mount Hagen - ORD
$7,750 → $963
88%
Found on March 27
Paderborn - ORD
$3,400 → $460
86%
Found on March 27
Twin Falls - ORD
$700 → $111
84%
Found on April 1
Cancún - ORD
$645 → $147
77%
Check these nearby airports too
Looking for more options? These airports near ORD sometimes drop rare deals too:
Kalamazoo/Battle Creek International (AZO)
~4 rare deals/month
General Mitchell International (MKE)
~7 rare deals/month
Chicago Rockford International (RFD)
~13 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially AZO and MKE for long-haul deal surprises.
When Is the Best Time to Fly from Tucson International 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
in the key of 3
City Winery Chicago, PUSH 365, and TrustLive Entertainment present In The Key of 3, featuring Joyce Hurley, Simbryt, and Simone Green live on Tuesday, March 31st at 7:30 PM. This is a night of incredible music and entertainment you won't want to miss.
catchlight
In partnership with ONA, the largest journalism conference in the country, and Borderless Magazine, this program features live storytelling by John Moore (Getty Images) and Camilla Forte, sharing powerful narratives and insights.
cards and conversation
Join us for an evening of card games, board games, and engaging conversation. All are welcome, especially new faces looking to connect and have some fun!
the posthumous trial of giulia tofana
Giulia Tofana is remembered as a murderer, poisoner, and witch, Italy’s most prolific serial killer and the infamous creator of the Aqua Tofana poison. Authorities pursued her for her deadly craft, shrouded in mystery and intrigue.
Chicago Weather
Weather in Chicago
Tue, Mar 31
75%
21° 2°
75%
Wed, Apr 1
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.
