$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 • May, 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, Apr 28 - Wed, Apr 29
Cheapest
New York (EWR) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - New York (EWR)
Frontier Airlines airlines • Direct
$433
$56
-$377
87%
Tue, Apr 21 - Wed, Apr 22
New York (EWR) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - New York (EWR)
Frontier Airlines airlines • Direct
$433
$56
-$377
87%
Tue, May 5 - Wed, May 6
Dallas (DFW) - Chicago (ORD)
Frontier Airlines airlines • Direct
Chicago (ORD) - Dallas (DFW)
Frontier Airlines airlines • Direct
$155
$56
-$99
64%
Tue, May 5 - Wed, May 6
New York (EWR) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - New York (EWR)
Frontier Airlines airlines • Direct
$433
$56
-$377
87%
Tue, Apr 14 - Wed, Apr 15
New York (EWR) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - New York (EWR)
Frontier Airlines airlines • Direct
$433
$56
-$377
87%
Tue, Apr 14 - Wed, Apr 15
Atlanta (ATL) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Atlanta (ATL)
Frontier Airlines airlines • Direct
$123
$56
-$67
54%
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
Tue, Wed
Based on the data, Sunday and Saturday are the best days to find flight deals for Chicago Midway International Airport. You're most likely to find cheaper flights on these days compared to others.
Avg. deal survival time
15.7 hours
Deals from Chicago Midway International airport typically survive for an average of 15.7 hours. This relatively short lifespan emphasizes the need for travelers to act quickly when they find an appealing offer.
Rare deal frequency
17 deals
We found 17 rare deals for Chicago Midway International Airport in the past month thanks to our sophisticated system. These rare deals, which include mistake fares, special promotions, or ultra-discounts, all earned an AI Deal Score of 90+.
Average price drop
-76%
The average price drop for flights arriving at Chicago Midway International Airport is 76.4%, which can translate into significant savings for travelers. This substantial price decrease makes Chicago Midway an attractive option for budget-conscious individuals looking to fly into the Chicago area.
Next 4 weeks: deal forecast
Chicago Midway International Airport: Next Month Flight Forecast
Based on current trends, flight prices to and from Chicago Midway International Airport are expected to remain relatively stable next month. There may be slight fluctuations, but no significant price drops or increases are anticipated.
Top 5 biggest price drops (last 3 months)
Found on March 7
Santa Cruz de la Sierra - MDW
$3,950 → $437
89%
Found on March 4
Ottawa - MDW
$1,700 → $283
83%
Found on March 6
São Paulo - MDW
$1,420 → $248
83%
Found on March 7
Dayton - MDW
$665 → $131
80%
Found on March 4
Kelowna - MDW
$1,180 → $264
78%
Check these nearby airports too
Looking for more options? These airports near MDW sometimes drop rare deals too:
Gerald R. Ford International (GRR)
~4 rare deals/month
General Mitchell International (MKE)
~14 rare deals/month
Chicago Rockford International (RFD)
~3 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
syleena johnson
Get last-minute concert tickets to see Syleena Johnson perform at City Winery in Chicago, IL.
house calls w/ bassel darwish
House Calls presents Venezuelan selector Tony Guerra with support from Bassel Darwish!
lizzy sunshine — the den theatre
Lizzy Sunshine is forced to perform her double act alone, resulting in a chaotic and hilarious comedy show exploring addiction.
malvada saturdays
Find tickets for Malvada Saturdays at Moe's Cantina in River North, Chicago, on February 28, 2026.
Chicago Weather
Weather in Chicago
Tue, Mar 10
25%
16° 5°
25%
Wed, Mar 11
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.
