$40 Chicago to Miami + 52 more deals
This week's best flight deals from O'Hare and Midway - save up to 78% on flights to the Caribbean, Europe, Asia, and more. Premium members get access to Business Class deals from $149.
Your weekly roundup of the best flight deals from Chicago's O'Hare (ORD) and Midway (MDW) airports is here. This week is packed with standout savings - we're talking $40 round-trips to Miami, sub-$100 flights to Cancun, and deeply discounted fares to Europe and Asia. We've scoured both airports to bring you the sharpest deals available right now. Prices move fast, so don't wait too long if something catches your eye.
✈️ This Week's Free Economy Deals from Chicago
Below you'll find the best budget economy deals grouped by region. All flights are direct unless otherwise noted, and prices are round-trip.
🇺🇸 Domestic US
Good Deal - ORD → Miami - Usually $40-$149, now just $40 round-trip (save 58%). Multiple Airlines. Apr 10 - Apr 15 (5 nights). Direct. Miami is sitting at a beautiful 22C while Chicago is still at 4C - hard to argue with that. Best dates to fly:
Apr 10 - Apr 15 | $40 | 5 days
Apr 10 - Apr 17 | $40 | 7 days
Apr 10 - Apr 20 | $40 | 10 days
Good Deal - ORD → Los Angeles - Usually $64-$179, now just $64 round-trip (save 47%). Multiple Airlines. Apr 18 - Apr 23 (5 nights). Direct. Weekend departure. Best dates to fly:
Apr 18 - Apr 23 | $64 | 5 days
Apr 18 - Apr 25 | $64 | 7 days
Apr 18 - Apr 28 | $64 | 10 days
Good Deal - ORD → San Francisco - Usually $119-$245, now just $119 round-trip (save 35%). Multiple Airlines. Apr 14 - Apr 19 (5 nights). Direct. Midweek departure, returns on Sunday. Best dates to fly:
Apr 14 - Apr 19 | $119 | 5 days
Apr 14 - Apr 21 | $119 | 7 days
Apr 14 - Apr 24 | $119 | 10 days
Good Deal - ORD → Seattle - Usually $119-$244, now just $119 round-trip (save 34%). Multiple Airlines. Apr 18 - Apr 23 (5 nights). Direct. Weekend departure. Best dates to fly:
Apr 18 - Apr 23 | $119 | 5 days
Apr 18 - Apr 25 | $119 | 7 days
Apr 18 - Apr 28 | $119 | 10 days
Good Deal - ORD → Toronto - Usually $85-$95, now just $85 round-trip (save 6%). Multiple Airlines. Jul 1 - Jul 6 (5 nights). Direct. Great timing near Independence Day weekend. Best dates to fly:
Jul 1 - Jul 6 | $85 | 5 days
Jul 1 - Jul 8 | $85 | 7 days
Jul 1 - Jul 11 | $85 | 10 days
Thinking about using miles for any of these domestic routes? Award Travel Finder tracks the best award redemptions daily - worth checking if you have points to burn.
Midway (MDW) Domestic Picks
Good Deal - MDW → Phoenix - Usually $48-$150, now just $48 round-trip (save 52%). Multiple Airlines. Apr 20 - Apr 25 (5 nights). Direct. Great value out of Midway. Best dates to fly:
Apr 20 - Apr 25 | $48 | 5 days
Apr 20 - Apr 27 | $48 | 7 days
Apr 20 - Apr 30 | $48 | 10 days
Good Deal - MDW → Las Vegas - Usually $129-$209, now just $129 round-trip (save 24%). Multiple Airlines. Apr 18 - Apr 23 (5 nights). Direct. Weekend departure from Midway. Best dates to fly:
Apr 18 - Apr 23 | $129 | 5 days
Apr 18 - Apr 25 | $129 | 7 days
Apr 18 - Apr 28 | $129 | 10 days
🌴 Caribbean & Mexico
Good Deal - ORD → Cancun - Usually $95-$221, now just $95 round-trip (save 40%). Multiple Airlines. Apr 5 - Apr 10 (5 nights). Direct. Cancun is at 26C - beach paradise with warm Caribbean waters. Weekend departure. Best dates to fly:
Apr 5 - Apr 10 | $95 | 5 days
Apr 5 - Apr 12 | $95 | 7 days
Apr 5 - Apr 15 | $95 | 10 days
Good Deal - ORD → San Juan - Usually $110-$291, now just $110 round-trip (save 45%). Multiple Airlines. Apr 9 - Apr 14 (5 nights). Direct. Best dates to fly:
Apr 9 - Apr 14 | $110 | 5 days
Apr 9 - Apr 16 | $110 | 7 days
Apr 9 - Apr 19 | $110 | 10 days
Good Deal - ORD → Montego Bay - Usually $138-$1,130, now just $138 round-trip (save 78%). Multiple Airlines. Apr 7 - Apr 12 (5 nights). Direct. Jamaica sunshine and reggae vibes at 27C - this is exceptional value. Best dates to fly:
Apr 7 - Apr 12 | $138 | 5 days
Apr 7 - Apr 14 | $138 | 7 days
Apr 7 - Apr 17 | $138 | 10 days
Good Deal - ORD → Punta Cana - Usually $156-$543, now just $156 round-trip (save 55%). Multiple Airlines. Apr 8 - Apr 13 (5 nights). Direct. Dominican Republic beach resorts at 27C. Best dates to fly:
Apr 8 - Apr 13 | $156 | 5 days
Apr 8 - Apr 15 | $156 | 7 days
Apr 8 - Apr 18 | $156 | 10 days
🇪🇺 Europe
Europe deals are plentiful from O'Hare this spring. These are all economy fares on direct flights - genuinely strong prices for transatlantic routes.
Good Deal - ORD → London Heathrow - Usually $484-$715, now just $484 round-trip (save 19%). Multiple Airlines. Mar 29 - Apr 1 (3 nights). Direct. Departing next week - act fast. Best dates to fly:
Mar 29 - Apr 1 | $484 | 3 days
Mar 29 - Apr 2 | $484 | 4 days
Mar 29 - Apr 3 | $484 | 5 days
Good Deal - ORD → Lisbon - Usually $497-$2,383, now just $497 round-trip (save 65%). Multiple Airlines. Mar 29 - Apr 1 (3 nights). Direct. Departing next week - this is an outstanding price for Lisbon. Best dates to fly:
Mar 29 - Apr 1 | $497 | 3 days
Mar 29 - Apr 2 | $497 | 4 days
Mar 29 - Apr 3 | $497 | 5 days
Good Deal - ORD → Madrid - Usually $305-$1,240, now just $305 round-trip (save 61%). Multiple Airlines. May 10 - May 13 (3 nights). Direct. One of the best-value European fares we've seen from Chicago in a while. Best dates to fly:
May 10 - May 13 | $305 | 3 days
May 10 - May 14 | $305 | 4 days
May 10 - May 15 | $305 | 5 days
Good Deal - ORD → Barcelona - Usually $323-$1,294, now just $323 round-trip (save 60%). Multiple Airlines. May 10 - May 13 (3 nights). Direct. Mediterranean beaches and culture await. Best dates to fly:
May 10 - May 13 | $323 | 3 days
May 10 - May 14 | $323 | 4 days
May 10 - May 15 | $323 | 5 days
Good Deal - ORD → Dublin - Usually $475-$590, now just $475 round-trip (save 11%). Multiple Airlines. Apr 19 - Apr 22 (3 nights). Direct. A quick spring break escape to Ireland. Best dates to fly:
Apr 19 - Apr 22 | $475 | 3 days
Apr 19 - Apr 23 | $475 | 4 days
Apr 19 - Apr 24 | $475 | 5 days
Good Deal - ORD → Paris - Usually $479-$831, now just $479 round-trip (save 27%). Multiple Airlines. May 10 - May 13 (3 nights). Direct. Spring in Paris at a great price. Best dates to fly:
May 10 - May 13 | $479 | 3 days
May 10 - May 14 | $479 | 4 days
May 10 - May 15 | $479 | 5 days
Good Deal - ORD → Rome - Usually $484-$910, now just $484 round-trip (save 31%). Multiple Airlines. Apr 19 - Apr 22 (3 nights). Direct. Best dates to fly:
Apr 19 - Apr 22 | $484 | 3 days
Apr 19 - Apr 23 | $484 | 4 days
Apr 19 - Apr 24 | $484 | 5 days
Good Deal - ORD → Amsterdam - Usually $599-$774, now just $599 round-trip (save 13%). Multiple Airlines. Apr 19 - Apr 22 (3 nights). Direct. Best dates to fly:
Apr 19 - Apr 22 | $599 | 3 days
Apr 19 - Apr 23 | $599 | 4 days
Apr 19 - Apr 24 | $599 | 5 days
Good Deal - ORD → Frankfurt - Usually $789-$1,769, now just $789 round-trip (save 38%). Multiple Airlines. May 10 - May 13 (3 nights). Direct. Best dates to fly:
May 10 - May 13 | $789 | 3 days
May 10 - May 14 | $789 | 4 days
May 10 - May 15 | $789 | 5 days
Good Deal - ORD → Munich - Usually $789-$1,894, now just $789 round-trip (save 41%). Multiple Airlines. May 10 - May 13 (3 nights). Direct. Best dates to fly:
May 10 - May 13 | $789 | 3 days
May 10 - May 14 | $789 | 4 days
May 10 - May 15 | $789 | 5 days
🌏 Asia-Pacific
Good Deal - ORD → Tokyo Narita - Usually $595-$1,277, now just $595 round-trip (save 36%). Multiple Airlines. Apr 12 - Apr 17 (5 nights). Direct. Spring in Tokyo - cherry blossom season is a magical time to visit. Weekend departure. Best dates to fly:
Apr 12 - Apr 17 | $595 | 5 days
Apr 12 - Apr 19 | $595 | 7 days
Apr 12 - Apr 22 | $595 | 10 days
Good Deal - ORD → Tokyo Haneda - Usually $645-$1,523, now just $645 round-trip (save 40%). Multiple Airlines. Apr 12 - Apr 17 (5 nights). Direct. Haneda is closer to central Tokyo than Narita - a great option. Best dates to fly:
Apr 12 - Apr 17 | $645 | 5 days
Apr 12 - Apr 19 | $645 | 7 days
Apr 12 - Apr 22 | $645 | 10 days
Good Deal - ORD → Hong Kong - Usually $704-$1,433, now just $704 round-trip (save 34%). Multiple Airlines. Apr 2 - Apr 7 (5 nights). Direct. Hong Kong is at a pleasant 19C - best in cooler months. Best dates to fly:
Apr 2 - Apr 7 | $704 | 5 days
Apr 2 - Apr 9 | $704 | 7 days
Apr 2 - Apr 12 | $704 | 10 days
Good Deal - ORD → Seoul - Usually $939-$2,544, now just $939 round-trip (save 46%). Multiple Airlines. Apr 6 - Apr 11 (5 nights). Direct. Best dates to fly:
Apr 6 - Apr 11 | $939 | 5 days
Apr 6 - Apr 13 | $939 | 7 days
Apr 6 - Apr 16 | $939 | 10 days
Good Deal - ORD → Delhi - Usually $1,066-$3,101, now just $1,066 round-trip (save 49%). Multiple Airlines. Apr 6 - Apr 11 (5 nights). Direct. Delhi at 23C - a great time to explore India. Best dates to fly:
Apr 6 - Apr 11 | $1,066 | 5 days
Apr 6 - Apr 13 | $1,066 | 7 days
Apr 6 - Apr 16 | $1,066 | 10 days
If you're eyeing any of these Asia routes with points instead of cash, Miles & Points Daily publishes the best credit card bonuses every day - a solid way to stack up points fast for your next big trip.
✈️ Chicago Airport Tip
O'Hare (ORD) is your go-to for almost all international routes - Europe, Asia-Pacific, the Middle East, and transatlantic deals all depart from ORD. Midway (MDW) shines for domestic budget routes - this week's Phoenix deal at $48 and Las Vegas at $129 are both from MDW and are Southwest and budget airline strong holds. If you're heading to the Caribbean or Mexico, check both airports as ORD sometimes offers nonstop options that MDW doesn't. For Tokyo, you have two airport options at O'Hare - Narita (NRT) and Haneda (HND). Haneda is generally more convenient for central Tokyo, though both are well served.
💼 Premium: Business Class & First Class Deals from Chicago
This week's premium cabin deals are stacked. We've got Business Class to Miami for just $149, transatlantic Business fares to Lisbon and Rome, and some deeply discounted flat-bed seats to Asia and the Middle East. Here's everything premium members need to know.
🇺🇸 Domestic Business Class
Good Deal - ORD → Miami (Business Class) - Usually $149-$486, now just $149 round-trip (save 53%). Multiple Airlines. Apr 19 - Apr 24 (5 nights). Direct. Business Class to Miami for under $150 is genuinely exceptional - that's barely more than economy on a normal day. Weekend departure. Best dates to fly:
Apr 19 - Apr 24 | $149 | 5 days
Apr 19 - Apr 26 | $149 | 7 days
Apr 19 - Apr 29 | $149 | 10 days
Good Deal - MDW → Phoenix (Business Class) - Usually $163-$279, now just $163 round-trip (save 26%). Multiple Airlines. Apr 19 - Apr 24 (5 nights). Direct from Midway. Best dates to fly:
Apr 19 - Apr 24 | $163 | 5 days
Apr 19 - Apr 26 | $163 | 7 days
Apr 19 - Apr 29 | $163 | 10 days
Good Deal - ORD → Los Angeles (Business Class) - Usually $173-$523, now just $173 round-trip (save 50%). Multiple Airlines. Apr 25 - Apr 30 (5 nights). Direct. Weekend departure. Best dates to fly:
Apr 25 - Apr 30 | $173 | 5 days
Apr 25 - May 2 | $173 | 7 days
Apr 25 - May 5 | $173 | 10 days
Good Deal - ORD → Seattle (Business Class) - Usually $289-$479, now just $289 round-trip (save 25%). Multiple Airlines. Apr 20 - Apr 25 (5 nights). Direct. Best dates to fly:
Apr 20 - Apr 25 | $289 | 5 days
Apr 20 - Apr 27 | $289 | 7 days
Apr 20 - Apr 30 | $289 | 10 days
Good Deal - ORD → San Francisco (Business Class) - Usually $428-$655, now just $428 round-trip (save 21%). Multiple Airlines. Apr 9 - Apr 14 (5 nights). Direct. Best dates to fly:
Apr 9 - Apr 14 | $428 | 5 days
Apr 9 - Apr 16 | $428 | 7 days
Apr 9 - Apr 19 | $428 | 10 days
🌴 Caribbean & Mexico Business Class
Good Deal - ORD → Cancun (Business Class) - Usually $196-$561, now just $196 round-trip (save 48%). Multiple Airlines. Apr 27 - May 2 (5 nights). Direct. Business Class to Cancun for under $200 is a superb deal. Best dates to fly:
Apr 27 - May 2 | $196 | 5 days
Apr 27 - May 4 | $196 | 7 days
Apr 27 - May 7 | $196 | 10 days
Good Deal - ORD → Punta Cana (Business Class) - Usually $287-$1,511, now just $287 round-trip (save 68%). Multiple Airlines. Apr 7 - Apr 12 (5 nights). Direct. Dominican Republic in Business Class for $287 - an outstanding deal. Best dates to fly:
Apr 7 - Apr 12 | $287 | 5 days
Apr 7 - Apr 14 | $287 | 7 days
Apr 7 - Apr 17 | $287 | 10 days
Good Deal - ORD → San Juan (Business Class) - Usually $307-$499, now just $307 round-trip (save 24%). Multiple Airlines. Jun 21 - Jun 26 (5 nights). Direct. Weekend departure. Best dates to fly:
Jun 21 - Jun 26 | $307 | 5 days
Jun 21 - Jun 28 | $307 | 7 days
Jun 21 - Jul 1 | $307 | 10 days
Good Deal - ORD → Montego Bay (Business Class) - Usually $433-$3,077, now just $433 round-trip (save 75%). Multiple Airlines. May 16 - May 21 (5 nights). Direct. Jamaica in Business Class for $433 - normally fares can hit $3,077. Weekend departure. Best dates to fly:
May 16 - May 21 | $433 | 5 days
May 16 - May 23 | $433 | 7 days
May 16 - May 26 | $433 | 10 days
🇪🇺 Europe Business Class
Good Deal - ORD → Rome (Business Class) - Usually $2,809-$13,934, now just $2,809 round-trip (save 66%). Multiple Airlines. Mar 31 - Apr 3 (3 nights). Direct. Departing next week. This is a significant saving on a premium flat-bed seat to Rome. Best dates to fly:
Mar 31 - Apr 3 | $2,809 | 3 days
Mar 31 - Apr 4 | $2,809 | 4 days
Mar 31 - Apr 5 | $2,809 | 5 days
Good Deal - ORD → Lisbon (Business Class) - Usually $2,989-$6,915, now just $2,989 round-trip (save 40%). Multiple Airlines. Apr 1 - Apr 4 (3 nights). Direct. Departing next week. Business Class to Lisbon with Mild 15C weather - ideal shoulder season timing. Best dates to fly:
Apr 1 - Apr 4 | $2,989 | 3 days
Apr 1 - Apr 5 | $2,989 | 4 days
Apr 1 - Apr 6 | $2,989 | 5 days
Good Deal - ORD → Dublin (Business Class) - Usually $3,714-$6,205, now just $3,714 round-trip (save 25%). Multiple Airlines. Apr 21 - Apr 24 (3 nights). Direct. Best dates to fly:
Apr 21 - Apr 24 | $3,714 | 3 days
Apr 21 - Apr 25 | $3,714 | 4 days
Apr 21 - Apr 26 | $3,714 | 5 days
Good Deal - ORD → London Heathrow (Business Class) - Usually $4,264-$9,334, now just $4,264 round-trip (save 37%). Multiple Airlines. Apr 21 - Apr 24 (3 nights). Direct. London Business Class at a substantial discount - normally creeps well above $9,000. Best dates to fly:
Apr 21 - Apr 24 | $4,264 | 3 days
Apr 21 - Apr 25 | $4,264 | 4 days
Apr 21 - Apr 26 | $4,264 | 5 days
Good Deal - ORD → Madrid (Business Class) - Usually $4,364-$13,944, now just $4,364 round-trip (save 52%). Multiple Airlines. May 5 - May 8 (3 nights). Direct. This is the biggest percentage saving in the European Business Class category - normally up to $13,944. Best dates to fly:
May 5 - May 8 | $4,364 | 3 days
May 5 - May 9 | $4,364 | 4 days
May 5 - May 10 | $4,364 | 5 days
Good Deal - ORD → Toronto (Business Class) - Usually $208-$371, now just $208 round-trip (save 28%). Multiple Airlines. Jun 1 - Jun 6 (5 nights). Direct. Business Class to Toronto around Memorial Day season. Best dates to fly:
Jun 1 - Jun 6 | $208 | 5 days
Jun 1 - Jun 8 | $208 | 7 days
Jun 1 - Jun 11 | $208 | 10 days
🌏 Asia-Pacific Business Class
Good Deal - ORD → Delhi (Business Class) - Usually $3,202-$7,402, now just $3,202 round-trip (save 40%). Multiple Airlines. Apr 20 - Apr 25 (5 nights). Direct. Best dates to fly:
Apr 20 - Apr 25 | $3,202 | 5 days
Apr 20 - Apr 27 | $3,202 | 7 days
Apr 20 - Apr 30 | $3,202 | 10 days
Good Deal - ORD → Tokyo Narita (Business Class) - Usually $3,384-$5,129, now just $3,384 round-trip (save 20%). Multiple Airlines. Jun 24 - Jun 29 (5 nights). Direct. Summer Business Class to Tokyo. Best dates to fly:
Jun 24 - Jun 29 | $3,384 | 5 days
Jun 24 - Jul 1 | $3,384 | 7 days
Jun 24 - Jul 4 | $3,384 | 10 days
Good Deal - ORD → Tokyo Haneda (Business Class) - Usually $3,384-$4,307, now just $3,384 round-trip (save 12%). Multiple Airlines. Jun 24 - Jun 29 (5 nights). Direct. Haneda airport is closer to central Tokyo. Best dates to fly:
Jun 24 - Jun 29 | $3,384 | 5 days
Jun 24 - Jul 1 | $3,384 | 7 days
Jun 24 - Jul 4 | $3,384 | 10 days
Good Deal - ORD → Seoul (Business Class) - Usually $3,640-$4,944, now just $3,640 round-trip (save 15%). Multiple Airlines. Jul 6 - Jul 11 (5 nights). Direct. Summer travel just after Independence Day. Best dates to fly:
Jul 6 - Jul 11 | $3,640 | 5 days
Jul 6 - Jul 13 | $3,640 | 7 days
Jul 6 - Jul 16 | $3,640 | 10 days
Good Deal - ORD → Hong Kong (Business Class) - Usually $4,239-$6,567, now just $4,239 round-trip (save 22%). Multiple Airlines. Apr 2 - Apr 7 (5 nights). Direct. Best dates to fly:
Apr 2 - Apr 7 | $4,239 | 5 days
Apr 2 - Apr 9 | $4,239 | 7 days
Apr 2 - Apr 12 | $4,239 | 10 days
Prefer redeeming miles for Business Class to Asia? Award Travel Finder monitors award availability daily and regularly surfaces Business Class redemptions to Tokyo, Seoul and Hong Kong at fantastic rates.
🌍 Middle East Business Class
Good Deal - ORD → Dubai (Business Class) - Usually $4,418-$8,554, now just $4,418 round-trip (save 32%). Multiple Airlines. Apr 2 - Apr 7 (5 nights). Direct. Dubai at 23C - desert warmth and luxury. Business Class at a substantial discount. Best dates to fly:
Apr 2 - Apr 7 | $4,418 | 5 days
Apr 2 - Apr 9 | $4,418 | 7 days
Apr 2 - Apr 12 | $4,418 | 10 days
Good Deal - ORD → Doha (Business Class) - Usually $10,295-$11,211, now just $10,295 round-trip (save 4%). Multiple Airlines. Jun 17 - Jun 22 (5 nights). Direct. Premium long-haul to Doha this summer. Best dates to fly:
Jun 17 - Jun 22 | $10,295 | 5 days
Jun 17 - Jun 24 | $10,295 | 7 days
Jun 17 - Jun 27 | $10,295 | 10 days
🏙️ Chicago Airport Strategies for Premium Travelers
O'Hare (ORD) is where all the long-haul action happens. Every international Business and First Class deal this week departs from ORD - it's home to major carriers including United Airlines (Terminal 1), American Airlines (Terminal 3), and international carriers in Terminal 5. For Business Class to Europe, United Polaris and British Airways out of ORD are the most frequently discounted. For Asia, ANA and Japan Airlines regularly offer competitive Business Class pricing from O'Hare.
Midway (MDW) punches above its weight for domestic Business Class - the Phoenix and Las Vegas premium cabin deals this week are excellent value. Southwest doesn't offer Business Class but their premium seating options can be had for less. For Caribbean Business Class, always compare ORD pricing first as Midway rarely beats it on premium fares.
For transatlantic Business Class: O'Hare Terminal 5 is your gateway - arrive 3 hours early for international departures
For Asia-Pacific Business: Terminal 1 and Terminal 5 handle most long-haul Asian carriers from ORD
For Caribbean and Mexico premium: Terminal 3 (American) and Terminal 1 (United) both have strong Caribbean networks
For domestic Business Class from Midway: MDW has efficient security and shorter walks to gates - a genuine advantage for quick domestic hops
Hidden gem tip: ORD to Toronto (YYZ) at $85 economy is a strong value play for a Canada city break - just 1.5 hours in the air
🎯 Award Deals We're Tracking
Award Travel Finder hunts down the best redemptions so you don't have to.
Hong Kong First Class for 150k Points + Easter Escape Deals Across 3 Regions
March 19, 2026
Business & First Class cabin deals, 12 hotel redemptions, transfer bonuses expiring soon, and why this week's Cathay availability is turning heads.
London to New York for 27,500 Points + British Airways Avios Bonanza
March 17, 2026
Easter availability is wide open, Hyatt is delivering 7.7cpp in the Caribbean, and Chase is handing out 20% bonus Avios right now.
London to NYC First Class for 80k Points + Marriott Free Night Upgrade & Citi Points Sharing Ends
March 14, 2026
Premium cabin deals across Europe, massive Hyatt hotel value, and all the transfer bonuses you need to book smarter this week
See all deals at AwardTravelFinder.com →