Book flights to Chicago. Chicago offers big-city culture, outdoor escapes and urban adventures all in one. Admire the vast waters of Lake Michigan from the Navy Pier, overlooked by more than 100 skyscrapers. Then, take a tour of some early examples of Art Deco architecture, which stand out against some of the world’s tallest buildings.1 2016-2020 Freddie Awards.. 2 First and second checked bags. Weight and size limits apply. 3 Fare difference may apply.. 4 Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.. 5 Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our …Find flights to Chicago from $197. Fly from Germany on TAP AIR PORTUGAL, British Airways, Scandinavian Airlines and more. Fly from Berlin from $197, from Düsseldorf from $292, from Munich from $295, from Hamburg from $321 or from Frankfurt am Main from $468. Search for Chicago flights on KAYAK now to find the best deal.Flight deals from Washington D.C. to Chicago. Looking for a cheap last-minute deal or the best return flight from Washington D.C. to Chicago? Find the lowest prices on one-way …Southwest Airlines and Delta fly from Washington to Chicago every 4 hours. Alternatively, Amtrak operates a train from Washington Union Station to Chicago Union Station once daily. Tickets cost $30 - $240 and the journey takes 17h 40m. Airlines. Southwest Airlines.Fly to Washington, D.C., with United Airlines from over 200 airports within the United States and an additional 100 airports internationally. Washington D.C.’s top attractions. Walk along the National Mall, a park stretching two miles in downtown featuring museums and memorials.Browse some of the best deals on flights to Chicago in 2024. More deals are always being added, so be sure to check back regularly. Tue 5/21 11:55 pm LAX - ORD. Nonstop 4h 05m Spirit Airlines. Wed 5/22 1:13 pm ORD - LAX. 1 stop 9h 34m Spirit Airlines. Deal found 4/17 $68. Pick Dates. Free entertainment and $8 Internet. Book flights from Washington, D.C. (Dulles) to Chicago (Midway) with Southwest Airlines®. Bundle your flight with a hotel or rental car booking and find even more savings. The cheapest return flight ticket from Chicago O'Hare Airport to Washington, D.C. found by KAYAK users in the last 72 hours was for $85 on Frontier, followed by Spirit Airlines ($102). One-way flight deals have also been found from as low as $43 on Frontier and from $59 on American Airlines. Are you searching for American Airlines flights from Washington, D.C. to Chicago? Find the best selections and fly in style. Each day, there are between 19 and 21 nonstop flights that take off from Chicago O'Hare Intl Airport and land in Washington, D.C. Reagan-National Airport, with an average flight time of 1h 52m. The most common departure time is 6:00 pm and most flights take off in the morning. Each week, there are 144 flights. Spirit Airlines is one of the most popular airlines used for those traveling from Washington, D.C. to Chicago. Flights on this route from Spirit Airlines typically cost $360.95 RT, a price that is 29% more expensive than the average Washington, D.C. to Chicago flight. The cheapest flight found was $276 RT. The cheapest month for flights from Chicago Midway Airport to Washington, D.C. Reagan-National Airport is January, where tickets cost $257 on average. On the other hand, the most expensive months are June and March, where the average cost of tickets is $363 and $326 respectively. Chicago. ₹ 2,548 per passenger.Departing Wed, 10 Apr.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Wed, 10 Apr, arriving in Chicago Midway.Price includes taxes and charges.From ₹ 2,548, select. Wed, 10 Apr BWI - MDW with Frontier Airlines.Book one-way or return flights from Washington D.C. to Chicago starting at US$37. Fly with top airlines and search for flights deals on Trip.com now! O'Hare Intl. flight + hotel packages - economy flights. $80 Search for cheap flights deals from IAD to ORD (Washington Dulles Intl. to O'Hare Intl.). We offer cheap direct, non-stop flights including one way and roundtrip tickets. The two airlines most popular with KAYAK users for flights from Chicago to Washington, D.C. are Delta and United Airlines. With an average price for the route of $276 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $308 and an overall rating of 7.4. The calculation of flight time is based on the straight line distance from Washington, DC to Chicago, IL ("as the crow flies"), which is about 595 miles or 957 kilometers. Your trip begins in Washington, District of Columbia. It ends in Chicago, Illinois. Your flight direction from Washington, DC to Chicago, IL is Northwest (-66 degrees from ... LondonHouse Chicago, Curio Collection by Hilton. Save 100% on your flight. $819. $555. per person. Apr 24 - Apr 28. Roundtrip non-stop flight included. Washington (DCA) to Chicago (ORD)Looking to fly from the United States to Chicago with United Airlines? 25% of our users found flights for the following prices or less: From Washington, D.C. Dulles Intl Airport $164 one-way, $298 round-trip; from South Bend $192 one-way, $382 round-trip; from San Jose $238 one-way, $454 round-trip. The cheapest return flight ticket from Chicago O'Hare Airport to Washington, D.C. found by KAYAK users in the last 72 hours was for $85 on Frontier, followed by Spirit Airlines ($102). One-way flight deals have also been found from as low as $43 on Frontier and from $59 on American Airlines. Use Google Flights to find cheap departing flights to Chicago and to track prices for specific travel dates for your next getaway.Flight tickets to Chicago start from £188 one-way. Flex your dates to secure the best fare for your Chicago O'Hare International airport flight. If your travel dates are flexible, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago O'Hare International airport from your chosen departure location.Cheap Flights from Dallas to Chicago (DFW-ORD) Prices were available within the past 7 days and start at $34 for one-way flights and $61 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Dallas to Chicago with no change fee on selected flights.Non-stop flights between Chicago, IL and Washington, DC. Here is a list of direct nonstop flights from Chicago, Illinois to Washington, District of Columbia. This can help you find the best flight on your preferred airline. We found a total of 3 flights to Washington, DC nonstop: Airline routes; American Airlines from ORD to BWI Prices were available within the past 7 days and start at $80 for one-way flights and $159 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to Washington with no change fee on selected flights. Earn your airline miles on top of our rewards! Direct. from $47. Chicago.$61 per passenger.Departing Mon, Apr 29, returning Wed, May 1.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Baltimore Washington International on Mon, Apr 29, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on ... Use Google Flights to explore cheap flights to anywhere. Search destinations and track prices to find and book your next flight.Direct. from £63. Washington D.C.. £89 per passenger.Departing Tue, 30 Apr, returning Wed, 1 May.Return flight with Spirit Airlines and Frontier Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 30 Apr, arriving in Baltimore Washington International.Inbound indirect flight with Frontier ...$89 Cheap Delta flights Chicago (ORD) to Washington (IAD) Prices were available within the past 7 days and start at $89 for one-way flights and $182 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.Flights ». Worldwide. $42. Flights to North America, Worldwide. Find flights to Worldwide from $24. Fly from Chicago on Frontier, Spirit Airlines and more. Search for Worldwide flights on KAYAK now to find the best deal.Non-stop flights between Chicago, IL and Washington, DC. Here is a list of direct nonstop flights from Chicago, Illinois to Washington, District of Columbia. This can help you find the best flight on your preferred airline. We found a total of 3 flights to Washington, DC nonstop: Airline routes; American Airlines from ORD to BWIBook flights from Washington, D.C. (Dulles) to Chicago (O'Hare) with Southwest Airlines ®. It’s easy to find the Washington Dulles International Airport to Chicago O'Hare International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you’ll enjoy ...There are 5 airlines that fly nonstop from Boston to Chicago. They are: American Airlines, Delta, JetBlue, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with JetBlue at $81 for a one-way flight. On average, the best prices for this route can be found at JetBlue.Prices were available within the past 7 days and start at $69 for one-way flights and $137 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. Book one-way or return flights from Chicago to Washington with no change fee on selected flights. Earn your airline miles on top of our rewards! Free entertainment and $8 Internet. Book flights from Washington, D.C. (Dulles) to Chicago (Midway) with Southwest Airlines®. Bundle your flight with a hotel or rental car booking and find even more savings. Book cheap flights to Washington, D.C. (IAD) with United Airlines. Enjoy all the in-flight perks on your Washington, D.C. flight, including speed Wi-Fi. Browse some of the best deals on flights to Chicago in 2024. More deals are always being added, so be sure to check back regularly. Tue 5/21 11:55 pm LAX - ORD. Nonstop 4h 05m Spirit Airlines. Wed 5/22 1:13 pm ORD - LAX. 1 stop 9h 34m Spirit Airlines. Deal found 4/17 $68. Pick Dates.$80 Search for cheap flights deals from ORD to IAD (O'Hare Intl. to Washington Dulles Intl.). We offer cheap direct, non-stop flights including one way and roundtrip tickets. Cheap Flights from Chicago to Washington (ORD-IAD) Prices were available within the past 7 days and start at $80 for one-way flights and $159 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals. Economy Flight + Hotel Deals. Find inexpensive Chicago (ORD) flights today with Orbitz. Flights to CHI start at $24. Some airlines are waiving change fees for new bookings as COVID-19 disrupts travel.Route Flight number. Apr 19, 2024. When? United Airlines (UA) Airline. Check status. Check the status of your United Airlines flight by searching by route or flight number. Stay up to date with our flight status tools.1 2016-2020 Freddie Awards.. 2 First and second checked bags. Weight and size limits apply. 3 Fare difference may apply.. 4 Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.. 5 Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our …Chicago. $103. Flights to Chicago Midway Airport, Chicago. $154. Flights to Chicago O'Hare Intl Airport, Chicago. Find flights to Chicago from $49. Fly from District of Columbia on American Airlines, United Airlines, Frontier and more. Search for Chicago flights on KAYAK now to find the best deal.Washington , DC , USA ORD Chicago Ohare International. Chicago , IL , USA CHANGE DIRECTION Flight time. 2h 35m. Flight distance. 614mi, 988km. ... All flights to Chicago are departing from terminal 2 at Washington (DCA). VIEW IN MAP EXPLORER. Non-stop flights from DCA to ORD 614 miles (988 km) · 2 hours and 35 minutes CHECK …The cheapest month for flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport is September, where tickets cost $204 on average. On the other hand, the most expensive months are May and December, where the average cost of tickets is $477 and $470 respectively. Amazing Delta DCA to ORD Flight Deals. The cheapest flights to O'Hare Intl. found within the past 7 days were $170 round trip and $88 one way. Prices and availability subject to change. Additional terms may apply. Sat, May 18 - Sat, May 18. Direct. from $47. Chicago.$61 per passenger.Departing Mon, Apr 29, returning Wed, May 1.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Baltimore Washington International on Mon, Apr 29, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on ...The average flying time for a direct flight from Washington DC, DC to Chicago is 2 hours 12 minutes. Most direct flights leave around 7:00 EDT. Southwest Airlines flight #878 is today's earliest flight from Washington DC, DC to Chicago (6:05 EDT, Boeing 737-700 (winglets) pax) Southwest Airlines flight #2038 is today's latest flight from ...Book United Airlines cheap flights to 300+ destinations worldwide on our official site. Find our most popular flight deals and earn MileagePlus® miles. ... Our main U.S. hubs are located in the major cities of Chicago, Denver, Houston, New York/Newark, Los Angeles, San Francisco and Washington, D.C. United is a founding member of Star Alliance ...Round-trip One-way. Wed 4/24. Wed 5/1. 1 adult, Economy. Find deals. We work with more than 300 partners to bring you better travel deals. The best prices from …Southwest Airlines and Delta fly from Washington to Chicago every 4 hours. Alternatively, Amtrak operates a train from Washington Union Station to Chicago Union Station once daily. Tickets cost $30 - $240 and the journey takes 17h 40m. Airlines. Southwest Airlines.First Class. $408. Chicago Midway Airport. $256. Chicago O'Hare Intl Airport. Search and compare first class flight deals to Chicago. Fly from New York from $394, from Dallas from $449, from New York from $461. Book your first class tickets to Chicago.The cheapest month for flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport is September, where tickets cost $204 on average. On the other hand, the most expensive months are May and December, where the average cost of tickets is $477 and $470 respectively.Book one-way or return flights from Washington D.C. to Chicago starting at US$37. Fly with top airlines and search for flights deals on Trip.com now!United runs flights every 60 minutes between Ohare and Regan, if there is a problem on one they get you on the next. Pay a little more now and be thankful. Statistically Spirit’s reliability is average. The issue is, however, they have a lot fewer flights if there is a problem, and they don’t rebook on other airlines.Cheap Flights from Washington to Chicago (DCA-ORD) Prices were available within the past 7 days and start at $80 for one-way flights and $159 for round trip, for the period …CHICAGO (AP) — Right-hander Kyle Hendricks and left-hander Drew Smyly were placed on the 15-day injured list by the Chicago Cubs before Tuesday night’s …Cheap Flights from Washington to Chicago (IAD-MDW) Prices were available within the past 7 days and start at $78 for one-way flights and $178 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals.Chicago. $63. Flights to Chicago Midway Airport, Chicago. $60. Flights to Chicago O'Hare Intl Airport, Chicago. Find flights to Chicago from $38. Fly from North Carolina on Frontier, Spirit Airlines and more. Search for Chicago flights on …In the Pacific Northwest in 2021, another heat wave resulted in some 600 excess deaths. “Heat is a threat to our health,” CDC director Mandy Cohen said at the …The average flying time for a direct flight from Washington DC, DC to Chicago is 2 hours 12 minutes. Most direct flights leave around 7:00 EDT. Southwest Airlines flight #878 is today's earliest flight from Washington DC, DC to Chicago (6:05 EDT, Boeing 737-700 (winglets) pax) Southwest Airlines flight #2038 is today's latest flight from ... How much is the cheapest flight to Chicago? Prices were available within the past 7 days and start at $31 for one-way flights and $57 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals. The average flight time from Chicago (Midway) to Washington, D.C. (Reagan National) is 1 hour 50 minutes. How many Southwest flights occur weekly from Chicago (Midway) to Washington, D.C. (Reagan National)? There are 106 weekly flights from Chicago (Midway) to Washington, D.C. (Reagan National) on Southwest Airlines. Washington DC Bureau. ... delayed flights by: Hannah Brandt. Posted: Apr 24, 2024 / 04:06 PM CDT. Updated: Apr 24, 2024 / 04:06 PM CDT. ... Chicago's Very …The two airlines most popular with KAYAK users for flights from Chicago to Baltimore are Delta and United Airlines. With an average price for the route of $266 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $335 and an overall rating of 7.4.Surge in complaints in 2022. The Biden Administration proposed its change to the refund rules in 2022 after a surge in complaints about refunds when the …Non-stop flights between Washington, DC and Chicago, IL. Here is a list of direct nonstop flights from Washington, District of Columbia to Chicago, Illinois. This can help you find the best flight on your preferred airline. We found a total of 5 flights to Chicago, IL nonstop: Airline routes; American Airlines from DCA to ORDConnect with us. Find low fares to top destinations on the official Southwest Airlines website. Book flight reservations, rental cars, and hotels on southwest.com.Book cheap flights from Washington DC to Chicago on CheapOair and enjoy great discounts. Whether its leisure or a business trip, we offer the most competitive rates on flight tickets to destinations around the world. Grab WAS to CHI flight deals on CheapOair and save big! Hurry, our cheap rates are not going to last forever, so make your ...Find airfare and ticket deals for cheap flights from Chicago, IL to Washington, D.C., DC. Search flight deals from various travel partners with one click at $39. Cheap Flights from Washington to Chicago (IAD-ORD) Prices were available within the past 7 days and start at $78 for one-way flights and $157 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals. There are 4 airlines that fly nonstop from Chicago to Washington, D.C.. They are: American Airlines, Frontier, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $67 for a one-way flight. On average, the best prices for this route can be found at Frontier. Amazing Delta DCA to ORD Flight Deals. The cheapest flights to O'Hare Intl. found within the past 7 days were $170 round trip and $88 one way. Prices and availability subject to change. Additional terms may apply. Sat, May 18 - Sat, May 18. Book cheap flights from Washington DC to Chicago on CheapOair and enjoy great discounts. Whether its leisure or a business trip, we offer the most competitive rates on flight tickets to destinations around the world. Grab WAS to CHI flight deals on CheapOair and save big! Hurry, our cheap rates are not going to last forever, so make your ... Looking to fly from the United States to Chicago with United Airlines? 25% of our users found flights for the following prices or less: From Washington, D.C. Dulles Intl Airport $164 one-way, $298 round-trip; from South Bend $192 one-way, $382 round-trip; from San Jose $238 one-way, $454 round-trip. Use Google Flights to explore cheap flights to anywhere. Search destinations and track prices to find and book your next flight.Use Google Flights to plan your next trip and find cheap one way or round trip flights from Chicago to anywhere in the world. Find the best flights fast, track prices, and book with confidence.Flights to Cape Canaveral, Florida. $139. Flights to Cape Coral, Florida. Flights to Cocoa Beach, Florida. $178. Flights to Daytona Beach, Florida. View more. Find flights to Florida from $30. Fly from Washington, D.C. on Frontier, Spirit Airlines and more. Book flights from Washington, D.C. (Reagan National) to Chicago (O'Hare) with Southwest Airlines ®. It’s easy to find the Ronald Reagan Washington National Airport to Chicago O'Hare International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you ... Average prices by travel date. $270 $180 $90 Apr Apr. Over the next 30 days, a one-way train trip from Washington DC to Chicago will cost between $151 and $269. Book in advance to secure the best price in the next few weeks.6 days ago · Find airfare and ticket deals for cheap flights from Chicago, IL to Washington, D.C., DC. Search flight deals from various travel partners with one click at $39. Use Google Flights to find cheap departing flights to Chicago and to track prices for specific travel dates for your next getaway.Change location. Change currency. Feedback. Help. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Washington, D.C. to anywhere in the world.Southwest Airlines and Delta fly from Washington to Chicago every 4 hours. Alternatively, Amtrak operates a train from Washington Union Station to Chicago Union Station once daily. Tickets cost $30 - $240 and the journey takes 17h 40m. Airlines. Southwest Airlines.Flights from Washington, D.C. (DCA) to Chicago (MDW) When the Windy City calls you away from the Capital Region, Southwest Airlines ® has you covered with direct flights … Cheap Flights from Chicago to Washington (ORD-IAD) Prices were available within the past 7 days and start at $80 for one-way flights and $159 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals. Fly to Washington, D.C., with United Airlines from over 200 airports within the United States and an additional 100 airports internationally. Washington D.C.’s top attractions. Walk along the National Mall, a park stretching two miles in downtown featuring museums and memorials.There are 4 airlines that fly nonstop from Denver to Chicago. They are: American Airlines, Frontier, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $25 for a one-way flight. On average, the best prices for this route can be found at Frontier.
Free entertainment and $8 Internet. Book flights from Washington, D.C. (Dulles) to Chicago (Midway) with Southwest Airlines®. Bundle your flight with a hotel or rental car booking and find even more savings. . Things to do within an hour of my location
Find airfare and ticket deals for cheap flights from Washington, D.C. Dulles Intl Airport (IAD) to Chicago, IL. Search flight deals from various travel partners with one click at $78.Flights ». Worldwide. $42. Flights to North America, Worldwide. Find flights to Worldwide from $24. Fly from Chicago on Frontier, Spirit Airlines and more. Search for Worldwide flights on KAYAK now to find the best deal.$80 Search for cheap flights deals from DCA to ORD (Ronald Reagan Washington National to O'Hare Intl.). We offer cheap direct, non-stop flights including one way and roundtrip tickets. ... May 15 from Washington to Chicago, returning Wed, May 22, priced at $159 just found. Wed, May 15 - Wed, May 22. DCA. Washington. ORD. Chicago. $159 … There are 3 airlines that fly nonstop from Washington, D.C. Reagan-National Airport to Chicago. They are: American Airlines, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at $162 for a one-way flight. On average, the best prices for this route can be found at American Airlines. First Class. $408. Chicago Midway Airport. $256. Chicago O'Hare Intl Airport. Search and compare first class flight deals to Chicago. Fly from New York from $394, from Dallas from $449, from New York from $461. Book your first class tickets to Chicago.JetBlue Route map lets you explore over 100 destinations in the U.S., Latin America and Caribbean, plus London, with low fares and great service. Whether you want to visit San Francisco, Boston, or any other city, you can find your deal and book your flight with our interactive map.Cheap Flights from Seattle to Chicago (SEA-ORD) Prices were available within the past 7 days and start at $64 for one-way flights and $134 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals.Flights from Washington, D.C. to Chicago. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Washington, D.C. to Chicago. Find the...Find airfare and ticket deals for cheap flights from Washington, D.C. Dulles Intl Airport (IAD) to Chicago, IL. Search flight deals from various travel partners with one click at $78. Washington to Chicago Flights. Flights from DCA to ORD are operated 74 times a week, with an average of 11 flights per day. Departure times vary between 05:59 - 21:00. The earliest flight departs at 05:59, the last flight departs at 21:00. However, this depends on the date you are flying so please check with the full flight schedule above to ... There are 4 airlines that fly nonstop from Denver to Chicago. They are: American Airlines, Frontier, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $25 for a one-way flight. On average, the best prices for this route can be found at Frontier.North America, Caribbean and Latin America premium cabin dining. United Economy dining. Special meals. Inflight beverage selection. About United. Products and services. Popular destinations. Select from the wide selection of inflight dining options United offers. Check out the menu selection as well as beverage options, healthy dining and more.Book flights from Chicago (O'Hare) to Washington, D.C. (Dulles) with Southwest Airlines ®. It’s easy to find the Chicago O'Hare International Airport to Washington Dulles International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you’ll enjoy ... The calculation of flight time is based on the straight line distance from Washington, DC to Chicago, IL ("as the crow flies"), which is about 595 miles or 957 kilometers. Your trip begins in Washington, District of Columbia. It ends in Chicago, Illinois. Your flight direction from Washington, DC to Chicago, IL is Northwest (-66 degrees from ... Non-stop flights between Chicago, IL and Washington, DC. Here is a list of direct nonstop flights from Chicago, Illinois to Washington, District of Columbia. This can help you find the best flight on your preferred airline. We found a total of 3 flights to Washington, DC nonstop: Airline routes; American Airlines from ORD to BWIfrom $48. Cheap flights to Chicago starting at $48. It’s no wonder the Windy City is one of the most popular destinations in the world with its impressive art museums, music festivals, delectable cuisine and popular sporting events. Allegiant Chicago vacation packages combine low-cost flights to Chicago with hotel deals and cheap car rentals. Direct. from $47. Chicago.$61 per passenger.Departing Mon, Apr 29, returning Wed, May 1.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Baltimore Washington International on Mon, Apr 29, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on ... The two airlines most popular with KAYAK users for flights from New York to Chicago are Southwest and Alaska Airlines. With an average price for the route of $281 and an overall rating of 8.2, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $328 and an overall rating of 8.1..