$28 Cheap Flights to Chicago
One-way
Departing from
United States
Going to
Chicago, United States
Chicago (MDW)
United States • May, 2026
93% AI deal score
$433 $28
Chicago (MDW)
United States • April, 2026
93% AI deal score
$433 $28
Chicago (MDW)
United States • April, 2026
93% AI deal score
$433 $28
Chicago (MDW)
United States • April, 2026
93% AI deal score
$433 $28
Top Cheap Flight Deals from United States to Chicago
Recent round-trip flight deals to Chicago
Tue, Mar 10 - Wed, Mar 11
Cheapest
Dallas (DFW) - Chicago (ORD)
Frontier Airlines airlines • Direct
Chicago (ORD) - Dallas (DFW)
Frontier Airlines airlines • Direct
$155
$46
-$109
70%
Sat, Apr 25 - Sat, May 2
Tampa (TPA) - Chicago (ORD)
Frontier Airlines airlines • Direct
Chicago (ORD) - Tampa (TPA)
Frontier Airlines airlines • Direct
$123
$46
-$77
63%
Sat, May 2 - Sat, May 16
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$170
$46
-$124
73%
Sat, Apr 25 - Sat, May 9
Tampa (TPA) - Chicago (ORD)
Frontier Airlines airlines • Direct
Chicago (ORD) - Tampa (TPA)
Frontier Airlines airlines • Direct
$123
$46
-$77
63%
Sat, Apr 25 - Sat, May 16
Tampa (TPA) - Chicago (ORD)
Frontier Airlines airlines • Direct
Chicago (ORD) - Tampa (TPA)
Frontier Airlines airlines • Direct
$123
$46
-$77
63%
Sat, Mar 7 - Sat, Apr 4
Orlando (MCO) - Chicago (ORD)
Frontier Airlines airlines • Direct
Chicago (ORD) - Orlando (MCO)
Frontier Airlines airlines • Direct
$168
$50
-$118
70%
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):
Facts About Flights from United States 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.
MDW Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
MDW airport insights
Best days to catch a deal
Mon, Sun
Based on the data, Tuesday is the best day to find cheap flight deals from Chicago Midway International Airport. You might also find some good deals on Friday or Saturday, as these days have the next lowest counts.
Avg. deal survival time
11.1 hours
Deals from Chicago Midway International Airport have an average survival time of 11.1 hours. So, you need to book fast if you see a deal you like from Chicago Midway International Airport.
Rare deal frequency
11 deals
We discovered 11 rare flight deals for Chicago Midway International Airport in the last month. These rare deals earned an AI Deal Score of 90+ and typically include mistake fares, special promotions, or ultra-discounts.
Average price drop
-85%
The average price drop for flights from Chicago Midway International Airport is an impressive 84.5%, indicating significant potential savings for travelers. With such a substantial price reduction, flying from this airport could be a budget-friendly option.
Next 4 weeks: deal forecast
Chicago Midway International Forecast
Based on current data, flight prices to Chicago Midway International are expected to remain relatively stable in March 2026. There are no significant price drops or increases anticipated at this time.
Top 5 biggest price drops (last 3 months)
Found on February 11
New York - MDW
$1,298 → $56
96%
Found on February 11
Angeles - MDW
$6,400 → $669
90%
Found on February 18
Bangkok - MDW
$4,825 → $592
88%
Found on February 16
Bridgetown - MDW
$5,450 → $760
86%
Found on February 16
Okinawa Island - MDW
$3,375 → $539
84%
Check these nearby airports too
Looking for more options? These airports near MDW sometimes drop rare deals too:
Gerald R. Ford International (GRR)
~14 rare deals/month
General Mitchell International (MKE)
~11 rare deals/month
Quad City International (MLI)
~10 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 from United States 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
avery sunshine
Get tickets to see Avery*Sunshine perform live at City Winery Chicago on January 31, 2026, at 9:30 PM.
best of the second city
Find tickets for Best of The Second City at UP Comedy Club in Chicago, Illinois on January 31, 2026. Experience the iconic comedy show with hilarious sketches and improvisations.
kumbia night
Get tickets for Kumbia Night at Lemon in Chicago, Illinois on January 31, 2026. Dance the night away to the infectious rhythms of Kumbia music.
house of wndr : wndr museum
Experience House of WNDR at the WNDR Museum, an immersive disco experience presented by RITUALS & SOLSTICE. Celebrate the Solstice with an evening of illuminating music, art, and energy.
Chicago Weather
Weather in Chicago
Tue, Feb 17
10%
13° 4°
10%
Wed, Feb 18
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.
