55 flight deals from Chicago (from $28)

Your weekly roundup of the best flight deals from Chicago's two airports - O'Hare (ORD) and Midway (MDW). This week we've spotted 55 deals across Economy and Business Class, with prices starting at just $28 round-trip. We've done the hard work so you don't have to - read on for the sharpest fares departing the Windy City right now.

This Week's Best Economy Deals from Chicago

All deals below are Economy class and open to every reader. Prices are round-trip unless noted. Deals are sorted by savings and value - act fast, these fares move quickly!

🇺🇸 Domestic US

Good Deal - MDW → Phoenix - $28 round-trip with Multiple Airlines. Usually $28-$168, now just $28 - save 71%. Departs Apr 27 (Monday), returns May 2 (Saturday). Direct flight. This is the headline deal of the week - an extraordinary low fare from Midway to Phoenix.

Best dates to fly:- Apr 27 - May 2 | $28 | 5 days- Apr 27 - May 4 | $28 | 7 days- Apr 27 - May 7 | $28 | 10 days

Good Deal - ORD → Miami - $44 round-trip with Multiple Airlines. Usually $44-$179, now just $44 - save 61%. Departs Apr 9 (Thursday), returns Apr 14 (Tuesday). Direct flight. Miami in spring at this price is a no-brainer - 22C at your destination vs 4C in Chicago!

Best dates to fly:- Apr 9 - Apr 14 | $44 | 5 days- Apr 9 - Apr 16 | $44 | 7 days- Apr 9 - Apr 19 | $44 | 10 days

Good Deal - ORD → Los Angeles - $47 round-trip with Multiple Airlines. Usually $47-$219, now just $47 - save 65%. Weekend departure Apr 18 (Saturday), returns Apr 23 (Thursday). Direct flight. LA for under $50 round-trip from O'Hare is exceptional value.

Best dates to fly:- Apr 18 - Apr 23 | $47 | 5 days- Apr 18 - Apr 25 | $47 | 7 days- Apr 18 - Apr 28 | $47 | 10 days

Good Deal - ORD → San Francisco - $107 round-trip with Multiple Airlines. Usually $107-$301, now just $107 - save 48%. Departs Apr 21 (Tuesday), returns Apr 26 (Sunday). Direct flight.

Best dates to fly:- Apr 21 - Apr 26 | $107 | 5 days- Apr 21 - Apr 28 | $107 | 7 days- Apr 21 - May 1 | $107 | 10 days

Good Deal - ORD → Seattle - $113 round-trip with Multiple Airlines. Usually $113-$232, now just $113 - save 34%. Departs Apr 21 (Tuesday), returns Apr 26 (Sunday). Direct flight.

Best dates to fly:- Apr 21 - Apr 26 | $113 | 5 days- Apr 21 - Apr 28 | $113 | 7 days- Apr 21 - May 1 | $113 | 10 days

Good Deal - MDW → Las Vegas - $113 round-trip with Multiple Airlines. Usually $113-$219, now just $113 - save 32%. Departs Apr 21 (Tuesday), returns Apr 26 (Sunday). Direct flight from Midway.

Best dates to fly:- Apr 21 - Apr 26 | $113 | 5 days- Apr 21 - Apr 28 | $113 | 7 days- Apr 21 - May 1 | $113 | 10 days

Good Deal - ORD → Toronto - $85 round-trip with Multiple Airlines. Usually $85-$224, now just $85 - save 45%. Departs May 6 (Wednesday), returns May 11 (Monday). Direct flight. A quick hop across the border at an excellent price.

Best dates to fly:- May 6 - May 11 | $85 | 5 days- May 6 - May 13 | $85 | 7 days- May 6 - May 16 | $85 | 10 days

🌴 Caribbean and Mexico

Good Deal - ORD → Cancun - $95 round-trip with Multiple Airlines. Usually $95-$176, now just $95 - save 30%. Weekend departure Apr 12 (Sunday), returns Apr 17 (Friday). Direct flight. 26C beach paradise with warm Caribbean waters - a steal from ORD.

Best dates to fly:- Apr 12 - Apr 17 | $95 | 5 days- Apr 12 - Apr 19 | $95 | 7 days- Apr 12 - Apr 22 | $95 | 10 days

Good Deal - ORD → San Juan, Puerto Rico - $99 round-trip with Multiple Airlines. Usually $99-$200, now just $99 - save 34%. Departs Jul 4 (Saturday - Independence Day weekend!), returns Jul 9 (Thursday). Direct flight. Celebrate the 4th of July in Puerto Rico for under $100!

Best dates to fly:- Jul 4 - Jul 9 | $99 | 5 days- Jul 4 - Jul 11 | $99 | 7 days- Jul 4 - Jul 14 | $99 | 10 days

Good Deal - ORD → Punta Cana - $138 round-trip with Multiple Airlines. Usually $138-$564, now just $138 - save 61%. Weekend departure Apr 11 (Saturday), returns Apr 16 (Thursday). Direct flight. Dominican Republic beach resorts at 27C - an outstanding deal.

Best dates to fly:- Apr 11 - Apr 16 | $138 | 5 days- Apr 11 - Apr 18 | $138 | 7 days- Apr 11 - Apr 21 | $138 | 10 days

Good Deal - ORD → Montego Bay, Jamaica - $138 round-trip with Multiple Airlines. Usually $138-$526, now just $138 - save 58%. Weekend departure Apr 12 (Sunday), returns Apr 17 (Friday). Direct flight. Jamaica sunshine and reggae vibes at 27C - in 2 weeks!

Best dates to fly:- Apr 12 - Apr 17 | $138 | 5 days- Apr 12 - Apr 19 | $138 | 7 days- Apr 12 - Apr 22 | $138 | 10 days

🇪🇺 Europe

Good Deal - ORD → Paris - $504 round-trip with Multiple Airlines. Usually $504-$650, now just $504 - save 13%. Departs Apr 7 (Tuesday - next week!), returns Apr 10 (Friday). Direct flight. A quick Paris long weekend departing very soon.

Best dates to fly:- Apr 7 - Apr 10 | $504 | 3 days- Apr 7 - Apr 11 | $504 | 4 days- Apr 7 - Apr 12 | $504 | 5 days

Good Deal - ORD → London Heathrow - $509 round-trip with Multiple Airlines. Usually $509-$559, now just $509 - save 5%. Weekend departure Apr 5 (Sunday - next week!), returns Apr 8 (Wednesday). Direct flight. A very short break to London departing this coming Sunday.

Best dates to fly:- Apr 5 - Apr 8 | $509 | 3 days- Apr 5 - Apr 9 | $509 | 4 days- Apr 5 - Apr 10 | $509 | 5 days

Good Deal - ORD → Rome - $509 round-trip with Multiple Airlines. Usually $509-$1,074, now just $509 - save 36%. Weekend departure Apr 19 (Sunday), returns Apr 22 (Wednesday). Direct flight. Rome in spring for $509 round-trip is exceptional value.

Best dates to fly:- Apr 19 - Apr 22 | $509 | 3 days- Apr 19 - Apr 23 | $509 | 4 days- Apr 19 - Apr 24 | $509 | 5 days

Good Deal - ORD → Barcelona - $513 round-trip with Multiple Airlines. Usually $513-$707, now just $513 - save 16%. Departs Apr 13 (Monday), returns Apr 16 (Thursday). Direct flight. Mediterranean beaches and culture in 2 weeks.

Best dates to fly:- Apr 13 - Apr 16 | $513 | 3 days- Apr 13 - Apr 17 | $513 | 4 days- Apr 13 - Apr 18 | $513 | 5 days

Good Deal - ORD → Dublin - $506 round-trip with Multiple Airlines. Usually $506-$686, now just $506 - save 15%. Weekend departure Apr 26 (Sunday), returns Apr 29 (Wednesday). Direct flight.

Best dates to fly:- Apr 26 - Apr 29 | $506 | 3 days- Apr 26 - Apr 30 | $506 | 4 days- Apr 26 - May 1 | $506 | 5 days

Good Deal - ORD → Madrid - $594 round-trip with Multiple Airlines. Usually $594-$1,958, now just $594 - save 53%. Departs May 25 (Monday, near Memorial Day), returns May 28 (Thursday). Direct flight. Make the most of the Memorial Day holiday window with a Madrid escape.

Best dates to fly:- May 25 - May 28 | $594 | 3 days- May 25 - May 29 | $594 | 4 days- May 25 - May 30 | $594 | 5 days

Good Deal - ORD → Amsterdam - $624 round-trip with Multiple Airlines. Usually $624-$1,179, now just $624 - save 31%. Weekend departure Apr 26 (Sunday), returns Apr 29 (Wednesday). Direct flight.

Best dates to fly:- Apr 26 - Apr 29 | $624 | 3 days- Apr 26 - Apr 30 | $624 | 4 days- Apr 26 - May 1 | $624 | 5 days

Thinking about booking one of these Europe flights with miles instead of cash? Award Travel Finder tracks the best award redemptions daily - you might be able to fly ORD to London or Paris for as few as 30,000 miles one-way in Economy.

🌏 Asia-Pacific

Good Deal - ORD → Tokyo Narita - $645 round-trip with Multiple Airlines. Usually $645-$1,532, now just $645 - save 41%. Weekend departure Apr 19 (Sunday), returns Apr 24 (Friday). Direct flight. Spring in Tokyo - cherry blossom season!

Best dates to fly:- Apr 19 - Apr 24 | $645 | 5 days- Apr 19 - Apr 26 | $645 | 7 days- Apr 19 - Apr 29 | $645 | 10 days

Good Deal - ORD → Tokyo Haneda - $645 round-trip with Multiple Airlines. Usually $645-$1,582, now just $645 - save 42%. Weekend departure Apr 19 (Sunday), returns Apr 24 (Friday). Direct flight. Same price as Narita - Haneda is closer to central Tokyo, so worth considering.

Best dates to fly:- Apr 19 - Apr 24 | $645 | 5 days- Apr 19 - Apr 26 | $645 | 7 days- Apr 19 - Apr 29 | $645 | 10 days

Good Deal - ORD → Hong Kong - $704 round-trip with Multiple Airlines. Usually $704-$1,200, now just $704 - save 26%. Departs Apr 9 (Thursday), returns Apr 14 (Tuesday). Direct flight. Hong Kong at 19C - perfect shoulder season weather.

Best dates to fly:- Apr 9 - Apr 14 | $704 | 5 days- Apr 9 - Apr 16 | $704 | 7 days- Apr 9 - Apr 19 | $704 | 10 days

Good Deal - ORD → Seoul - $989 round-trip with Multiple Airlines. Usually $989-$2,594, now just $989 - save 45%. Departs Apr 9 (Thursday), returns Apr 14 (Tuesday). Direct flight. Seoul in spring for under $1,000 round-trip is a strong deal.

Best dates to fly:- Apr 9 - Apr 14 | $989 | 5 days- Apr 9 - Apr 16 | $989 | 7 days- Apr 9 - Apr 19 | $989 | 10 days

Pro tip: If you're collecting miles for a future Asia trip, Miles and Points Daily covers the best credit card sign-up bonuses every single day - a strong welcome offer could earn enough miles for a free Business Class flight to Tokyo or Seoul.

Chicago Airport Tip

Choosing between O'Hare (ORD) and Midway (MDW)? Here's a quick guide this week: Midway is your best friend for domestic bargains - the MDW to Phoenix deal at $28 and MDW to Las Vegas at $113 are Midway-exclusive finds worth checking. O'Hare dominates for international routes - every Europe, Asia-Pacific, and Middle East deal this week departs from ORD. As a general rule, Midway is quicker to reach from the south and west sides of Chicago, while O'Hare is better connected to the North Shore and suburbs. Always check both airports before booking - sometimes the price difference is significant!

Premium: Business Class and First Class Deals from Chicago

This week's premium section is loaded with Business Class deals across domestic US, the Caribbean, Europe, the Middle East, and Asia-Pacific. Many of these are 30-66% below typical Business Class fares - remarkable savings for lie-flat seats and premium service. Here are the best of the bunch.

Business Class - Domestic US

Good Deal - MDW → Phoenix (Business) - $127 round-trip Business Class. Usually $127-$268, now just $127 - save 36%. Departs Apr 27 (Monday), returns May 2 (Saturday). Direct flight from Midway. Business Class to Phoenix for $127 round-trip is almost unheard of.

Best dates to fly:- Apr 27 - May 2 | $127 | 5 days- Apr 27 - May 4 | $127 | 7 days- Apr 27 - May 7 | $127 | 10 days

Good Deal - ORD → Miami (Business) - $153 round-trip Business Class. Usually $153-$489, now just $153 - save 52%. Departs Apr 20 (Monday), returns Apr 25 (Saturday). Direct. Beach weather in Miami (22C) in Business Class for $153 - an exceptional value.

Best dates to fly:- Apr 20 - Apr 25 | $153 | 5 days- Apr 20 - Apr 27 | $153 | 7 days- Apr 20 - Apr 30 | $153 | 10 days

Good Deal - ORD → Los Angeles (Business) - $161 round-trip Business Class. Usually $161-$289, now just $161 - save 28%. Weekend departure May 2 (Saturday), returns May 7 (Thursday). Direct.

Best dates to fly:- May 2 - May 7 | $161 | 5 days- May 2 - May 9 | $161 | 7 days- May 2 - May 12 | $161 | 10 days

Good Deal - ORD → Seattle (Business) - $297 round-trip Business Class. Usually $297-$478, now just $297 - save 23%. Departs Apr 16 (Thursday), returns Apr 21 (Tuesday). Direct.

Good Deal - ORD → San Francisco (Business) - $428 round-trip Business Class. Usually $428-$778, now just $428 - save 29%. Departs Apr 16 (Thursday), returns Apr 21 (Tuesday). Direct.

Business Class - Caribbean and Mexico

Good Deal - ORD → Cancun (Business) - $194 round-trip Business Class. Usually $194-$416, now just $194 - save 36%. Departs May 11 (Monday), returns May 16 (Saturday). Direct. Cancun in Business Class for under $200 is a standout deal.

Best dates to fly:- May 11 - May 16 | $194 | 5 days- May 11 - May 18 | $194 | 7 days- May 11 - May 21 | $194 | 10 days

Good Deal - ORD → Punta Cana (Business) - $307 round-trip Business Class. Usually $307-$1,511, now just $307 - save 66%. Departs Apr 13 (Monday), returns Apr 18 (Saturday). Direct. Saving up to $1,204 off typical prices - one of the best Business Class value deals this week.

Best dates to fly:- Apr 13 - Apr 18 | $307 | 5 days- Apr 13 - Apr 20 | $307 | 7 days- Apr 13 - Apr 23 | $307 | 10 days

Good Deal - ORD → San Juan (Business) - $218 round-trip Business Class. Usually $218-$388, now just $218 - save 28%. Weekend departure Jul 4 (Saturday - Independence Day!), returns Jul 9 (Thursday). Direct.

Good Deal - ORD → Montego Bay (Business) - $426 round-trip Business Class. Usually $426-$1,430, now just $426 - save 54%. Weekend departure Apr 19 (Sunday), returns Apr 24 (Friday). Direct. Jamaica in Business Class, saving over $500 off typical fares.

Business Class - Europe

Good Deal - ORD → Toronto (Business) - $198 round-trip Business Class. Usually $198-$337, now just $198 - save 26%. Departs May 6 (Wednesday), returns May 11 (Monday). Direct.

Good Deal - ORD → Rome (Business) - $2,834 round-trip Business Class. Usually $2,834-$7,392, now just $2,834 - save 45%. Departs Apr 21 (Tuesday), returns Apr 24 (Friday). Direct. Saving up to $2,279 off typical Business Class fares to Rome.

Best dates to fly:- Apr 21 - Apr 24 | $2,834 | 3 days- Apr 21 - Apr 25 | $2,834 | 4 days- Apr 21 - Apr 26 | $2,834 | 5 days

Good Deal - ORD → Lisbon (Business) - $3,039 round-trip Business Class. Usually $3,039-$7,065, now just $3,039 - save 40%. Departs Apr 3 (Friday - next week!), returns Apr 6 (Monday). Direct. A premium weekend break to Lisbon, saving over $2,000 off typical fares. Act fast - this one departs very soon.

Best dates to fly:- Apr 3 - Apr 6 | $3,039 | 3 days- Apr 3 - Apr 7 | $3,039 | 4 days- Apr 3 - Apr 8 | $3,039 | 5 days

Good Deal - ORD → Dublin (Business) - $3,739 round-trip Business Class. Usually $3,739-$6,230, now just $3,739 - save 25%. Departs Apr 28 (Tuesday), returns May 1 (Friday). Direct.

Good Deal - ORD → London Heathrow (Business) - $4,289 round-trip Business Class. Usually $4,289-$9,359, now just $4,289 - save 37%. Departs Apr 28 (Tuesday), returns May 1 (Friday). Direct. Saving up to $2,535 off typical Transatlantic Business Class fares.

Good Deal - ORD → Madrid (Business) - $4,664 round-trip Business Class. Usually $4,664-$14,019, now just $4,664 - save 50%. Departs May 5 (Tuesday), returns May 8 (Friday). Direct. Half the typical price for Business Class to Madrid - saving nearly $4,700.

Good Deal - ORD → Barcelona (Business) - $6,219 round-trip Business Class. Usually $6,219-$13,959, now just $6,219 - save 38%. Departs Apr 28 (Tuesday), returns May 1 (Friday). Direct. For a true luxury Barcelona escape, this is 38% below the typical fare.

Business Class - Middle East

Good Deal - ORD → Dubai (Business) - $4,418 round-trip Business Class. Usually $4,418-$8,554, now just $4,418 - save 32%. Departs Apr 9 (Thursday), returns Apr 14 (Tuesday). Direct. Dubai desert luxury in Business Class, saving over $2,000 off typical fares.

Best dates to fly:- Apr 9 - Apr 14 | $4,418 | 5 days- Apr 9 - Apr 16 | $4,418 | 7 days- Apr 9 - Apr 19 | $4,418 | 10 days

Good Deal - ORD → Doha (Business) - $10,295 round-trip Business Class. Usually $10,295-$12,220, now just $10,295 - save 9%. Departs Jun 24 (Wednesday), returns Jun 29 (Monday). Direct. Premium long-haul travel to Doha in summer.

Business Class - Asia-Pacific

Good Deal - ORD → Delhi (Business) - $3,202 round-trip Business Class. Usually $3,202-$7,402, now just $3,202 - save 40%. Departs May 18 (Monday), returns May 23 (Saturday, near Memorial Day). Direct. Saving over $2,100 off typical fares.

Best dates to fly:- May 18 - May 23 | $3,202 | 5 days- May 18 - May 25 | $3,202 | 7 days- May 18 - May 28 | $3,202 | 10 days

Good Deal - ORD → Tokyo Narita (Business) - $3,434 round-trip Business Class. Usually $3,434-$4,529, now just $3,434 - save 14%. Departs Jun 24 (Wednesday), returns Jun 29 (Monday). Direct.

Good Deal - ORD → Tokyo Haneda (Business) - $3,434 round-trip Business Class. Usually $3,434-$4,334, now just $3,434 - save 12%. Departs Jun 24 (Wednesday), returns Jun 29 (Monday). Direct. Same price as Narita - Haneda is the more convenient Tokyo airport.

Good Deal - ORD → Seoul (Business) - $3,690 round-trip Business Class. Usually $3,690-$4,994, now just $3,690 - save 15%. Departs Jul 6 (Monday, near Independence Day), returns Jul 11 (Saturday). Direct.

Good Deal - ORD → Hong Kong (Business) - $4,239 round-trip Business Class. Usually $4,239-$8,595, now just $4,239 - save 34%. Departs Apr 9 (Thursday), returns Apr 14 (Tuesday). Direct. Saving over $2,100 off typical Hong Kong Business Class fares.

Best dates to fly:- Apr 9 - Apr 14 | $4,239 | 5 days- Apr 9 - Apr 16 | $4,239 | 7 days- Apr 9 - Apr 19 | $4,239 | 10 days

Love the idea of flying Business Class to Tokyo, Seoul, or Hong Kong but would rather pay with miles? Award Travel Finder scours award space daily and regularly finds Business Class seats to Asia from Chicago for 70,000-90,000 miles one-way. Well worth checking before you pay cash.

Chicago Airport Strategies for Premium Travelers

For premium cabin travelers departing Chicago, O'Hare (ORD) is overwhelmingly the better choice. Every single Business Class and international deal this week departs from ORD - it's the gateway for United, American, British Airways, Lufthansa, Air France, and virtually every major carrier operating transatlantic and transpacific routes. Midway is excellent for budget domestic trips (and that remarkable $127 Business Class fare to Phoenix), but for Europe, Asia, and the Middle East in premium cabins, always check O'Hare first.

• ORD - Best for: All international routes, Business and First Class, Europe and Asia-Pacific, Star Alliance and oneworld hubs

• MDW - Best for: Budget domestic fares (Southwest Airlines stronghold), quick hops to Phoenix, Las Vegas, and Florida

• Transit tip for ORD: Allow at least 90 minutes for connections - it's a large airport. The Blue Line CTA runs directly to the terminal.

• Transit tip for MDW: 30-45 minutes is usually enough for connections. The Orange Line CTA is a quick and cheap ride from the Loop.

• Hidden gem: MDW often has competitive Southwest fares not shown on Google Flights - always check Southwest.com separately for MDW routes.

Want to stay on top of the best points strategies to complement these deals? Miles and Points Daily delivers the freshest credit card bonuses, transfer deals, and points news every single day - essential reading for any Chicago traveler looking to maximize every dollar spent on these flights.

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