Enjoy our travel experiences and fly in style! Find American Airlines flights to Japan and book your trip! ... Chicago (ORD) to. Tokyo (HND) 05/21/24 - 05/28/24. from. $1,315* Updated: 2 hours ago. Round trip. I. Economy. See Latest Fare. Chicago (ORD) to. Tokyo (TYO) 04/30/24 - 05/07/24. from. $1,265* Are you searching for American Airlines flights from Washington, D.C. to Chicago? Find the best selections and fly in style. Find flights to Romania from $396. Fly from Chicago on United Airlines, Turkish Airlines, Delta and more. Search for Romania flights on KAYAK now to find the best deal. 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. Aero. Launched in 2020, the semi-private, luxury airline Aero offers a slightly more elevated product than JSX, at more elevated prices. One-way flights from Dallas to Aspen start at $1,000, one-way flights from L.A. to Los Cabos start at $1,800, and one-way flights from London to Nice start at $1,600.The two airlines most popular with KAYAK users for flights from Washington, D.C. to Duluth are Delta and United Airlines. With an average price for the route of $446 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 $506 and an overall rating of 7.4.Airfares from $29 One Way, $58 Round Trip from Chicago to Washington. Prices starting at $58 for return flights and $29 for one-way flights to Washington were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply. Wed, May 1 - Wed, May 8. MDW. Chicago. BWI.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.There are 5 airlines that fly nonstop from Seattle to Chicago. They are: Alaska Airlines, American Airlines, Delta, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with Delta at $98 for a one-way flight. On average, the best prices for this route can be found at Alaska Airlines.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 …Enjoy our travel experiences and fly in style! Find American Airlines flights to Japan and book your trip! ... Chicago (ORD) to. Tokyo (HND) 05/21/24 - 05/28/24. from. $1,315* Updated: 2 hours ago. Round trip. I. Economy. See Latest Fare. Chicago (ORD) to. Tokyo (TYO) 04/30/24 - 05/07/24. from. $1,265*Take a cheap flight to Chicago and enjoy a fun weekend in a town with great nightlife. The Buddha Lounge offers is a great place to dance or just kick back and listen to DJs mixing world, electric, soul, funk, hip-hop, and more. A flight to Chicago is a great way to take a break from a busy schedule at any time during the year.Find flights to Chicago O'Hare Airport from $59. Fly from Reagan Washington National Airport on Frontier, American Airlines, United Airlines and more. Search for Chicago …This time of year offers the best deals on train tickets from Washington DC to Chicago, with the average price at just $179. Train tickets on this route are most expensive in July, when the average price goes up to $251. You can still score cheap deals below this average price, though, especially if you plan ahead and book your ticket in advance.Francis Tapon. After a few days in DC, it was time to take Amtrak to Chicago. Although the 18-hour journey seems daunting, I was looking forward to it because the trip would be in a Superliner ...The 745-mile road trip from Washington DC to Chicago will take 12 hours and 10 minutes to drive. On the way, you can visit Bedford, Somerset, Pittsburgh, Cleveland, Toledo, Boonsboro, Morgantown, Columbus, Cincinnati, Indianapolis and Lafayette. This incredible journey from Washington DC to Chicago is dotted with so …Midway sits on the southwest side of Chicago, eight miles from the Loop (downtown Chicago’s central business district). O’Hare is located on the far northwest side of the city, about 17 miles from the Loop. It’s easy to get into the city from both airports with service from Chicago Transit Authority’s L Trains. Flight deals from Washington, D.C. to Chicago. Looking for a cheap last-minute deal or the best round-trip flight from Washington, D.C. to Chicago? Find the lowest prices on one-way and round-trip tickets right here. 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 ... Subway to Washington Dulles, fly to Chicago O'Hare • 4h 44m. Take the subway from Farragut West, Blue/Orange/Silver Line Track 2 Platform to Washington Dulles International Airport, Silver Line Center Platform. Fly from Washington Dulles (IAD) to Chicago O'Hare (ORD) IAD - ORD. $124 - $561. Use Google Flights to explore cheap flights to anywhere. Search destinations and track prices to find and book your next flight.Use this map to view all of our available routes and flight options. To find travel requirements and pricing for our featured destinations, visit Explore Top Destinations. To Zoom Map, Mac - Press command key + finger scroll. Windows - …Fly to the US with Porter and discover what this beautiful country has to offer. Boston. Massachusetts Chicago. Illinois Fort Lauderdale. Florida Fort Myers. Florida Las Vegas. Nevada Los Angeles. California Miami. Florida New York - Newark.City Pair Program (CPP) The OMB-designated Best-in-Class City Pair Program procures and manages discounted air passenger transportation services for federal government travelers. At its inception in 1980 this service covered only 11 markets, and now covers over 13,000 markets. Today, CPP offers four different contract fares.There are 5 airlines that fly nonstop from Chicago to Miami. They are: American Airlines, Frontier, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $56 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines.Cheap Flights from Washington to Chicago (DCA-CHI) Prices were available within the past 7 days and start at $69 for one-way flights and $137 for round trip, for the period …Flights to Champaign, Illinois. $48. Flights to Chicago, Illinois. $289. Flights to Decatur, Illinois, Illinois. Find flights to Illinois from $36. Fly from Washington, D.C. on Frontier, Spirit Airlines and more. Search for Illinois flights on KAYAK now to find the best deal.Challenger 604. Seats. 10. Price. $18,200. Private flights to and from Chicago, IL with evoJets. Global private travel provider since 2006, A+ rating on BBB. Call (877) 970-5387 today!Find flights to Chicago from $34. Fly from Washington, D.C. on Frontier, Spirit Airlines and more. Search for Chicago flights on KAYAK now to find the best deal.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.$60 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. ... Select United flight, departing Thu, Jul 4 from Washington to Chicago, returning Thu, Jul 4, priced at $137 found 1 day ago. Wed, Apr 24 - Wed, May 1. DCA ...Once you've arrived, Chicago's vibrant live-music scene of jazz, blues and rock, along with its terrifically good-value culinary offerings and world-famous comedy clubs, will have you planning your next visit before your round-trip flight even leaves the tarmac. 7. Fly from Washington D.C. to Boston for as low as $142 round tripThe following Oneworld airlines also fly to Italy: British Airways flies from its hub in London-Heathrow (LHR) and London-Gatwick (LGW) to Rome, and from Heathrow to Milan and Venice. Finnair flies from Helsinki (HEL) to Milan, Venice and Rome. Iberia flies from Madrid (MAD) to Milan, Venice and Rome.Airfares from $29 One Way, $58 Round Trip from Chicago to Washington. Prices starting at $58 for return flights and $29 for one-way flights to Washington were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply. Wed, May 1 - Wed, May 8. MDW. Chicago. BWI.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.Our data shows that the cheapest route for a one-way flight from Washington, D.C. to San Francisco cost $193 and was between Baltimore and San Francisco. On average, the best prices are found if you fly from Washington, D.C. Dulles Intl Airport to San Francisco. The average price for a return flight for this route is $328.Baltimore may be Charm City, but you'll see that Chicago is just as charming. When you fly in from the D.C./Baltimore Area, you'll deplane at Chicago Midway International Airport on the Southwest side of Chicago. Unlike the East Coast, where everything's exceptionally close together, the Midwest has a little more room to stretch. Book cheap flights to Chicago (ORD) with United Airlines. Enjoy all the in-flight perks on your Chicago flight, including speed Wi-Fi. Airfares from $29 One Way, $58 Round Trip from Chicago to Washington. Prices starting at $58 for return flights and $29 for one-way flights to Washington were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply. Wed, May 1 - Wed, May 8. MDW. Chicago. BWI.Flying time between cities. Travelmath provides an online flight time calculator for all types of travel routes. You can enter airports, cities, states, countries, or zip codes to find the flying time between any two points. The database uses the great circle distance and the average airspeed of a commercial airliner to figure out how long a ...The total driving distance from Chicago, IL to Washington, DC is 699 miles or 1 125 kilometers. Your trip begins in Chicago, Illinois. It ends in Washington, District of Columbia. If you are planning a road trip, you might also want to calculate the total driving time from Chicago, IL to Washington, DC so you can see when you'll arrive at your ...Finnair. You can fly to London with Finnair from Los Angeles, Chicago, Boston, New York, and Washington DC. This domestic and international airline has its HQ in Helsinki, Finland. Founded in 1923, it’s one of the oldest airlines in the world—fun fact: back then, it was then known as Aero.This is a list of all destinations and flights from Washington (DCA) with Delta Airlines. Airline IATA code: DL. Aircrafts used: Code 220, Airbus A31X/32X, Boeing 757 More. Terminal: 2. Found 17 routes with direct flights from Washington with Delta Airlines. Show all airlines instead.Aero. Launched in 2020, the semi-private, luxury airline Aero offers a slightly more elevated product than JSX, at more elevated prices. One-way flights from Dallas to Aspen start at $1,000, one-way flights from L.A. to Los Cabos start at $1,800, and one-way flights from London to Nice start at $1,600.Economy. 08/14/24 - 08/19/24. from. $ 442*. Viewed: 15 hours ago. Top ↑. United offers the best deals on flights to Kalispell (FCA) to visit Glacier National Park. Book your next adventure today and save! Airfares from $29 One Way, $58 Round Trip from Chicago to Washington. Prices starting at $58 for return flights and $29 for one-way flights to Washington were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply. Wed, May 1 - Wed, May 8. MDW. Chicago. BWI. 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 best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $47. The fastest flight from Washington, D.C. to Chicago takes 1h 37m. …Challenger 604. Seats. 10. Price. $18,200. Private flights to and from Chicago, IL with evoJets. Global private travel provider since 2006, A+ rating on BBB. Call (877) 970-5387 today!Fly to Columbia, South Carolina, with United Airlines from over 200 airports within the United States and an additional 100 airports internationally. Columbia’s top attractions Visit the Hampton-Preston Mansion and Gardens, a historic house that has been a private residence, governor’s mansion, Union Army headquarters, convent and educational …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...fly for about 1.5 hours in the air. 8:32 pm (local time): Chicago O'Hare International (ORD) Chicago is 1 hour behind Washington, DC. so the time in Washington, DC is actually 9:32 pm. taxi on the runway for an average of 12 minutes to the gate. 8:44 pm (local time): arrive at the gate at ORD. deboard the plane, and claim any baggage. The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Delta and United Airlines. With an average price for the route of $246 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 $324 and an overall rating of 7.4. The cheapest way to get from Chicago to Washington, DC costs only $86, and the quickest way takes just 3 hours. Find the travel option that best suits you. ... The best way to get from Chicago to Washington, DC is to fly which takes 4h 11m and costs $85 - $330. Alternatively, you can train via Rockville Amtrak, which costs $30 - $240 and takes ...All flights from Chicago to London Gatwick. See airlines, aircrafts, flight time and distance, flight schedules and timetables. EN. ... Douglas DC-9. Embraer 170. Embraer 170/190. Embraer 175. Embraer 175. Embraer 190. Embraer 195. Embraer E190-E2. Embraer E195-E2. Embraer EMB.110 Bandeirnate.Fly to Columbia, South Carolina, with United Airlines from over 200 airports within the United States and an additional 100 airports internationally. Columbia’s top attractions Visit the Hampton-Preston Mansion and Gardens, a historic house that has been a private residence, governor’s mansion, Union Army headquarters, convent and educational …This time of year offers the best deals on train tickets from Washington DC to Chicago, with the average price at just $247. Train tickets on this route are most expensive in July, when the average price goes up to $346. You can still score cheap deals below this average price, though, especially if you plan ahead and book your ticket in advance.Find flights to Chicago O'Hare Airport from $59. Fly from Reagan Washington National Airport on Frontier, American Airlines, United Airlines and more. Search for Chicago …Cheap Flights from Washington to Chicago (DCA-CHI) Prices were available within the past 7 days and start at $69 for one-way flights and $137 for round trip, for the period …There are 5 airlines that fly nonstop from Chicago to Miami. They are: American Airlines, Frontier, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $56 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines. Subway to Washington Dulles, fly to Chicago O'Hare • 4h 44m. Take the subway from Farragut West, Blue/Orange/Silver Line Track 2 Platform to Washington Dulles International Airport, Silver Line Center Platform. Fly from Washington Dulles (IAD) to Chicago O'Hare (ORD) IAD - ORD. $124 - $561. Search airline tickets & flights to more than 900 destinations worldwide from the world-class airlines in the oneworld Alliance. Book round-trip or one-way.Fly to Columbia, South Carolina, with United Airlines from over 200 airports within the United States and an additional 100 airports internationally. Columbia’s top attractions Visit the Hampton-Preston Mansion and Gardens, a historic house that has been a private residence, governor’s mansion, Union Army headquarters, convent and educational …Airfares from $29 One Way, $58 Round Trip from Chicago to Washington. Prices starting at $58 for return flights and $29 for one-way flights to Washington were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply. Wed, May 1 - Wed, May 8. MDW. Chicago. BWI.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.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.Featured daily fares for flights from Washington, D.C. (IAD) to Chicago (ORD) … Subway to Washington Dulles, fly to Chicago O'Hare • 4h 44m. Take the subway from Farragut West, Blue/Orange/Silver Line Track 2 Platform to Washington Dulles International Airport, Silver Line Center Platform. Fly from Washington Dulles (IAD) to Chicago O'Hare (ORD) IAD - ORD. $124 - $561. Cheap Flights from DCA to ORD starting at $60 One Way, $139 Round Trip. Prices starting at $139 for return flights and $60 for one-way flights to O'Hare Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply. Wed, Apr 24 - Wed, May 1.Check out Scott's cheap flights. Free version. They will post good deals from various places. Since you live in the Midwest you may need to get the cheap flight from DC or NYC, than buy your ticket from home to that location. Normally can get flights from DC to Europe in the 500-700 range (and sometimes cheaper). 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. Book one-way or return flights from Washington to Chicago with no change fee on selected ... Destin (VPS) to Chicago (Midway) (MDW) flights from $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 … On average, a flight to Chicago O'Hare Intl Airport costs $411. The cheapest price found on KAYAK in the last 2 weeks cost $33 and departed from Atlanta. The most popular routes on KAYAK are New York to Chicago O'Hare Intl Airport which costs $282 on average, and Boston to Chicago O'Hare Intl Airport, which costs $395 on average. There are 3 airlines that fly nonstop from Chicago O'Hare Intl Airport to Washington, D.C.. They are: American Airlines, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at $147 for a one-way flight. On average, the best prices for this route can be found at American Airlines.Roundtrip. Tue, Aug 6 - Tue, Aug 13.It's no secret that the flights to Australia & New Zealand from the United States are long. Stopping for a night or longer along the way helps break up the trip and adds another destination to your travels.Airfares from $29 One Way, $58 Round Trip from Chicago to Washington. Prices starting at $58 for return flights and $29 for one-way flights to Washington were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply. Wed, May 1 - Wed, May 8. MDW. Chicago. BWI.Fill out the Alternative Airlines search form. Choose a return, one way or multi-city search. Enter the airports you want to fly between. Enter the dates you want to fly on. Select the number of travelers and preferred cabin class. Click ' Search Flights '. How to Book Red Eye Flight Tickets. Use the 'Times' filter.Flight distance = 437 miles one-way. Driving distance = 520 miles one-way. flying is faster. Getting to YYZ airport = 38 minutes. Toronto Pearson International Airport. Check-in/wait at the airport = 60 minutes. Flight time = 1 hour, 22 minutes. Chicago O'Hare International Airport. Leaving ORD airport = 48 minutes. There are 106 weekly flights from Chicago (Midway) to Washington, D.C. (Reagan National) on Southwest Airlines. Does Southwest fly nonstop on weekdays from Chicago (Midway) to Washington, D.C. (Reagan National)? Yes, Southwest flies nonstop from Chicago (Midway) to Washington, D.C. (Reagan National) 6 times per day from Monday through Friday. Find cheap flights from Reagan Washington National Airport to Chicago from $55. Round-trip. 1 adult. Economy. 0 bags. Add hotel. Sat 5/18. Sat 5/25. Search. Direct flights only. …$105. Book now. * Restrictions and exclusions apply. Seats and dates are limited. Select markets. 54 travel days available. Check out Washington, D.C. (Reagan National) to …and leave at 12:13 am (past midnight) drive for about 2 hours. 2:23 am (past midnight) Middlebury (Indiana) stay for about 1 hour. and leave at 3:23 am (past midnight) drive for about 2 hours. 5:34 am (next morning) arrive in Chicago. stay at The James Chicago Hotel. driving ≈ 13 hours.
Find flights to Chicago from $29. Fly from the United States on Frontier, Spirit Airlines and more. Fly from Dallas from $29, from Boston from $36, from Los Angeles from $42 or from New York from $46. Search for Chicago flights on KAYAK now to find the best deal.. Oralando to miami
Fly to the US with Porter and discover what this beautiful country has to offer. Boston. Massachusetts Chicago. Illinois Fort Lauderdale. Florida Fort Myers. Florida Las Vegas. Nevada Los Angeles. California Miami. Florida New York - Newark.Look out for flights from United Kingdom, this is the cheapest location to depart from when flying to Chicago O'Hare International airport. Compare flight deals to Chicago O'Hare International airport from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from £191 one-way.Find your vacation package to Chicago with United Packages. Book cheap flights to Chicago (ORD) with United Airlines. Enjoy all the in-flight perks on your Chicago flight, including speed Wi-Fi.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. 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 Washington to Chicago with no change fee on selected flights. Earn your airline miles on top of our rewards! Top cities between Chicago and Washington DC. The top cities between Chicago and Washington DC are Cleveland, Pittsburgh, Gettysburg, Detroit, Sandusky, Toledo, Luray, Holland, Ann Arbor, and South Bend. Cleveland is the most popular city on the route. It's 5 hours from Chicago and 6 hours from Washington DC.If you're flying from Washington D.C., the cheapest airport near Chicago is Chicago Midway – which is 9.0 miles away from the centre of Chicago. We've found flights into this airport … Flights from Washington (DCA) to Chicago (ORD) Origin airport. Ronald Reagan Washington National. Destination airport. O'Hare Intl. Airlines serving. Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, United. Popular airline. JetBlue Airways. Book flights to Europe with United. Book tickets to Europe with United and experience everything the historically rich continent has to offer. The diversity found throughout the European countries serves as a cornerstone to Western culture and caters to the desires of every type of traveler. Your flights to Europe will take you on a journey to ...There are 5 non-stop flights from Washington, District of Columbia to Chicago, Illinois. American Airlines. Southwest Airlines. Spirit Airlines. United Airlines. See the full list of airline routes and airports to book your trip. You may need to drive to a nearby airport to get a direct flight. Use the form below to search for cheap airline ...This is a list of all destinations and flights from Washington (DCA) with Delta Airlines. Airline IATA code: DL. Aircrafts used: Code 220, Airbus A31X/32X, Boeing 757 More. Terminal: 2. Found 17 routes with direct flights from Washington with Delta Airlines. Show all airlines instead.Top cities between Chicago and Washington DC. The top cities between Chicago and Washington DC are Cleveland, Pittsburgh, Gettysburg, Detroit, Sandusky, Toledo, Luray, Holland, Ann Arbor, and South Bend. Cleveland is the most popular city on the route. It's 5 hours from Chicago and 6 hours from Washington DC.The two airlines most popular with KAYAK users for flights from Washington, D.C. to Duluth are Delta and United Airlines. With an average price for the route of $446 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 $506 and an overall rating of 7.4.Flight time from IAD to ORD. Flying time between Washington Dulles International Airport, Washington, DC and Chicago O'hare International Airport, Chicago, Il. One stop & 1+ stop flight time between IAD & ORD. Washington, DC Airport to Chicago, Il …Wed, May 8 MDW – BWI with Frontier Airlines. Direct. from $59. Chicago.$60 per passenger.Departing Wed, Oct 2, returning Wed, Oct 9.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Baltimore Washington International on Wed, Oct 2, arriving in Chicago Midway.Inbound direct flight with ...Puerto Rico. One of the cheapest Caribbean destinations to visit through next year is the sunny capital city of Puerto Rico, San Juan. This low-cost tropical paradise is known for its colonial ...Find flights to Chicago from $29. Fly from the United States on Frontier, Spirit Airlines and more. Fly from Dallas from $29, from Boston from $36, from Los Angeles from $42 or from New York from $46. Search for Chicago flights on KAYAK now to find the best deal.Flights from Chicago to Washington, D.C.. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Chicago to Washington, D.C..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.and leave at 12:13 am (past midnight) drive for about 2 hours. 2:23 am (past midnight) Middlebury (Indiana) stay for about 1 hour. and leave at 3:23 am (past midnight) drive for about 2 hours. 5:34 am (next morning) arrive in Chicago. stay at The James Chicago Hotel. driving ≈ 13 hours..