Chicago Flight Deals - Fly to Miami for Just $28 Round-Trip This Week
Incredible fares from ORD and MDW - plus Business Class steals and warm escapes unlocked for Premium members
Your weekly roundup of the best flight deals from Chicago's O'Hare (ORD) and Midway (MDW) airports. This week we have 57 verified deals across Economy and Business Class - including one of the lowest domestic fares we have ever seen out of Chicago. Grab a coffee and scroll through before these disappear.
🌴 Chase the Sun This Winter
It is February in Chicago and that means one thing - grey skies, frozen sidewalks, and a serious need to escape. The good news? You can be on a warm beach for almost nothing this year. Here are the best warm-weather deals departing Chicago right now.
Miami - $28 round-trip 21°C average. Beach weather without the flight time - this is the headline deal of the week and one of the cheapest fares we have ever tracked out of Chicago.
Cancun - $94 round-trip 25°C average. Beach paradise with warm Caribbean waters - a stunning fare for a proper tropical escape from O'Hare.
Punta Cana - $103 round-trip 26°C average. Dominican Republic beach resorts at a price that is hard to believe - 55% below typical fares.
Montego Bay - $118 round-trip 27°C average. Jamaica sunshine and reggae vibes - this is 72% below what you would normally pay. Extraordinary.
Dubai - $586 round-trip 20°C average. Desert warmth and luxury - a solid long-haul warm escape at 35% below typical pricing.
🇺🇸 Domestic US Deals
Some genuinely jaw-dropping domestic fares this week from both O'Hare and Midway. These are direct flights at prices that rival a bus ticket.
ORD - Miami - $28 round-trip - Multiple Airlines. Apr 20 - Apr 25 (5 nights). Direct. ✅ Good Deal - 56% below typical ($28-$98).
Best dates to fly:
Apr 20 - Apr 25 | $28 | 5 days
Apr 20 - Apr 27 | $28 | 7 days
Apr 20 - Apr 30 | $28 | 10 days
MDW - Phoenix - $28 round-trip - Multiple Airlines. Apr 24 - Apr 29 (5 nights). Direct. ✅ Good Deal - 74% below typical ($28-$189). Departing on a Friday - perfect for a long weekend.
Best dates to fly:
Apr 24 - Apr 29 | $28 | 5 days
Apr 24 - May 1 | $28 | 7 days
Apr 24 - May 4 | $28 | 10 days
ORD - Los Angeles - $43 round-trip - Multiple Airlines. Apr 11 - Apr 16 (5 nights). Direct. ✅ Good Deal - 50% below typical ($43-$128). Weekend departure on Saturday.
Best dates to fly:
Apr 11 - Apr 16 | $43 | 5 days
Apr 11 - Apr 18 | $43 | 7 days
Apr 11 - Apr 21 | $43 | 10 days
ORD - San Francisco - $89 round-trip - Multiple Airlines. Apr 7 - Apr 12 (5 nights). Direct. ✅ Good Deal - 31% below typical ($89-$170). Midweek departure.
Best dates to fly:
Apr 7 - Apr 12 | $89 | 5 days
Apr 7 - Apr 14 | $89 | 7 days
Apr 7 - Apr 17 | $89 | 10 days
MDW - Las Vegas - $90 round-trip - Multiple Airlines. Apr 7 - Apr 12 (5 nights). Direct. ✅ Good Deal - 40% below typical ($90-$209). A great Midway option for Sin City fans.
Best dates to fly:
Apr 7 - Apr 12 | $90 | 5 days
Apr 7 - Apr 14 | $90 | 7 days
Apr 7 - Apr 17 | $90 | 10 days
ORD - Seattle - $99 round-trip - Multiple Airlines. Mar 19 - Mar 24 (5 nights). Direct. ✅ Good Deal - 44% below typical ($99-$253). Coming up in 3-4 weeks - act fast.
Best dates to fly:
Mar 19 - Mar 24 | $99 | 5 days
Mar 19 - Mar 26 | $99 | 7 days
Mar 19 - Mar 29 | $99 | 10 days
Pro tip: Many of these domestic deals can also be booked with miles. If you want to stack points on top of cheap fares or find award availability on the same routes, Award Travel Finder tracks the best award flight redemptions daily - well worth bookmarking.
🌴 Caribbean and Mexico Deals
Beyond the headline Miami deal, there are some exceptional Caribbean fares this week. These warm-weather escapes are priced well below what we typically see from Chicago.
ORD - Cancun - $94 round-trip - Multiple Airlines. Apr 15 - Apr 20 (5 nights). Direct. ✅ Good Deal - 38% below typical ($94-$207). 25°C average - beach paradise with warm Caribbean waters.
Best dates to fly:
Apr 15 - Apr 20 | $94 | 5 days
Apr 15 - Apr 22 | $94 | 7 days
Apr 15 - Apr 25 | $94 | 10 days
ORD - San Juan - $98 round-trip - Multiple Airlines. Jun 24 - Jun 29 (5 nights). Direct. ✅ Good Deal - 40% below typical ($98-$229). A great summer Puerto Rico trip.
Best dates to fly:
Jun 24 - Jun 29 | $98 | 5 days
Jun 24 - Jul 1 | $98 | 7 days
Jun 24 - Jul 4 | $98 | 10 days
ORD - Punta Cana - $103 round-trip - Multiple Airlines. Apr 13 - Apr 18 (5 nights). Direct. ✅ Good Deal - 55% below typical ($103-$351). 26°C average - Dominican Republic beach resorts.
Best dates to fly:
Apr 13 - Apr 18 | $103 | 5 days
Apr 13 - Apr 20 | $103 | 7 days
Apr 13 - Apr 23 | $103 | 10 days
ORD - Montego Bay - $118 round-trip - Multiple Airlines. Mar 24 - Mar 29 (5 nights). Direct. ✅ Good Deal - 72% below typical ($118-$737). 27°C average - Jamaica sunshine and reggae vibes. This one is in 3-4 weeks so move quickly.
Best dates to fly:
Mar 24 - Mar 29 | $118 | 5 days
Mar 24 - Mar 31 | $118 | 7 days
Mar 24 - Apr 3 | $118 | 10 days
🇪🇺 Europe Deals
Europe is wide open this spring from O'Hare, with solid deals to Paris, London, Rome, Madrid, Lisbon, Barcelona, Amsterdam, Frankfurt, Dublin, and Munich. Here are the standout Economy fares.
ORD - Paris - $394 round-trip - Multiple Airlines. May 10 - May 13 (3 nights). Direct. ✅ Good Deal - 30% below typical ($394-$731). Weekend departure - perfect for a short Paris break.
Best dates to fly:
May 10 - May 13 | $394 | 3 days
May 10 - May 14 | $394 | 4 days
May 10 - May 15 | $394 | 5 days
ORD - London Heathrow - $399 round-trip - Multiple Airlines. Mar 8 - Mar 11 (3 nights). Direct. ✅ Good Deal - 39% below typical ($399-$912). Next week - a seriously last-minute long weekend in London.
Best dates to fly:
Mar 8 - Mar 11 | $399 | 3 days
Mar 8 - Mar 12 | $399 | 4 days
Mar 8 - Mar 13 | $399 | 5 days
ORD - Rome - $399 round-trip - Multiple Airlines. Apr 15 - Apr 18 (3 nights). Direct. ✅ Good Deal - 30% below typical ($399-$749).
Best dates to fly:
Apr 15 - Apr 18 | $399 | 3 days
Apr 15 - Apr 19 | $399 | 4 days
Apr 15 - Apr 20 | $399 | 5 days
ORD - Dublin - $406 round-trip - Multiple Airlines. Mar 29 - Apr 1 (3 nights). Direct. ✅ Good Deal - 43% below typical ($406-$1,007). Weekend departure for a quick Dublin getaway.
Best dates to fly:
Mar 29 - Apr 1 | $406 | 3 days
Mar 29 - Apr 2 | $406 | 4 days
Mar 29 - Apr 3 | $406 | 5 days
ORD - Madrid - $415 round-trip - Multiple Airlines. Mar 8 - Mar 11 (3 nights). Direct. ✅ Good Deal - 64% below typical ($415-$1,873). One of the best savings percentages in this entire newsletter.
Best dates to fly:
Mar 8 - Mar 11 | $415 | 3 days
Mar 8 - Mar 12 | $415 | 4 days
Mar 8 - Mar 13 | $415 | 5 days
ORD - Lisbon - $418 round-trip - Multiple Airlines. Mar 8 - Mar 11 (3 nights). Direct. ✅ Good Deal - 52% below typical ($418-$1,318). Mild year-round, best in shoulder seasons.
Best dates to fly:
Mar 8 - Mar 11 | $418 | 3 days
Mar 8 - Mar 12 | $418 | 4 days
Mar 8 - Mar 13 | $418 | 5 days
ORD - Barcelona - $419 round-trip - Multiple Airlines. Apr 15 - Apr 18 (3 nights). Direct. ✅ Good Deal - 29% below typical ($419-$759). Mediterranean beaches and culture await.
Best dates to fly:
Apr 15 - Apr 18 | $419 | 3 days
Apr 15 - Apr 19 | $419 | 4 days
Apr 15 - Apr 20 | $419 | 5 days
ORD - Amsterdam - $524 round-trip - Multiple Airlines. Apr 7 - Apr 10 (3 nights). Direct. ✅ Good Deal - 21% below typical ($524-$799).
Best dates to fly:
Apr 7 - Apr 10 | $524 | 3 days
Apr 7 - Apr 11 | $524 | 4 days
Apr 7 - Apr 12 | $524 | 5 days
ORD - Frankfurt - $664 round-trip - Multiple Airlines. Apr 19 - Apr 22 (3 nights). Direct. ✅ Good Deal - 22% below typical ($664-$1,044). Weekend departure.
Best dates to fly:
Apr 19 - Apr 22 | $664 | 3 days
Apr 19 - Apr 23 | $664 | 4 days
Apr 19 - Apr 24 | $664 | 5 days
ORD - Munich - $664 round-trip - Multiple Airlines. Apr 19 - Apr 22 (3 nights). Direct. ✅ Good Deal - 22% below typical ($664-$1,044). Same weekend dates as Frankfurt - a great alternative.
Best dates to fly:
Apr 19 - Apr 22 | $664 | 3 days
Apr 19 - Apr 23 | $664 | 4 days
Apr 19 - Apr 24 | $664 | 5 days
🌏 Asia-Pacific Deals
Long-haul deals to Asia are looking excellent this week. Tokyo is a standout with spring cherry blossom season approaching, and Delhi is priced well below average for a destination of that distance.
ORD - Delhi - $290 round-trip - Multiple Airlines. Mar 16 - Mar 21 (5 nights). Direct. ✅ Good Deal - 43% below typical ($290-$731). 17°C - great time to visit. In 2 weeks, so this is urgent.
Best dates to fly:
Mar 16 - Mar 21 | $290 | 5 days
Mar 16 - Mar 23 | $290 | 7 days
Mar 16 - Mar 26 | $290 | 10 days
ORD - Tokyo Narita - $520 round-trip - Multiple Airlines. Apr 12 - Apr 17 (5 nights). Direct. ✅ Good Deal - 39% below typical ($520-$1,182). Spring cherry blossoms season - weekend departure.
Best dates to fly:
Apr 12 - Apr 17 | $520 | 5 days
Apr 12 - Apr 19 | $520 | 7 days
Apr 12 - Apr 22 | $520 | 10 days
ORD - Tokyo Haneda - $520 round-trip - Multiple Airlines. Apr 7 - Apr 12 (5 nights). Direct. ✅ Good Deal - 42% below typical ($520-$1,288). Midweek departure for cherry blossom season.
Best dates to fly:
Apr 7 - Apr 12 | $520 | 5 days
Apr 7 - Apr 14 | $520 | 7 days
Apr 7 - Apr 17 | $520 | 10 days
ORD - Hong Kong - $535 round-trip - Multiple Airlines. Mar 30 - Apr 4 (5 nights). Direct. ✅ Good Deal - 15% below typical ($535-$731). 17°C - best in cooler months.
Best dates to fly:
Mar 30 - Apr 4 | $535 | 5 days
Mar 30 - Apr 6 | $535 | 7 days
Mar 30 - Apr 9 | $535 | 10 days
Thinking about booking Tokyo or Hong Kong with points instead? Miles and Points Daily breaks down the best credit card bonuses every day - many of which can get you enough miles for a round-trip to Asia faster than you might think.
✈️ Chicago Airport Tip
This week's deals break down clearly by airport. O'Hare (ORD) is your best bet for long-haul routes - all Europe, Asia, and Middle East deals depart from ORD this week. Midway (MDW) is punching well above its weight for domestic travel, with exceptional $28 fares to Phoenix and $90 fares to Las Vegas. If you are heading somewhere in the US and live on the south or west side of Chicago, check Midway first - you can save on parking, transport, and the flight itself.
🇨🇦 Canada
ORD - Toronto - $85 round-trip - Multiple Airlines. Mar 25 - Mar 30 (5 nights). Direct. ✅ Good Deal - 59% below typical ($85-$328). In 3-4 weeks - a quick and affordable hop across the border.
Best dates to fly:
Mar 25 - Mar 30 | $85 | 5 days
Mar 25 - Apr 1 | $85 | 7 days
Mar 25 - Apr 4 | $85 | 10 days
Dubai Economy also makes an appearance in the free tier this week - see the Middle East section below.
🕌 Middle East Deals
ORD - Dubai - $586 round-trip - Multiple Airlines. Mar 15 - Mar 20 (5 nights). Direct. ✅ Good Deal - 35% below typical ($586-$1,231). 20°C average - desert warmth and luxury. Coming up in 2 weeks.
Best dates to fly:
Mar 15 - Mar 20 | $586 | 5 days
Mar 15 - Mar 22 | $586 | 7 days
Mar 15 - Mar 25 | $586 | 10 days
ORD - Tel Aviv - $669 round-trip - Multiple Airlines. Mar 31 - Apr 5 (5 nights). Direct. ✅ Good Deal - 27% below typical ($669-$1,159).
Best dates to fly:
Mar 31 - Apr 5 | $669 | 5 days
Mar 31 - Apr 7 | $669 | 7 days
Mar 31 - Apr 10 | $669 | 10 days
ORD - Doha - $690 round-trip - Multiple Airlines. Mar 16 - Mar 21 (5 nights). Direct. ✅ Good Deal - 23% below typical ($690-$1,094). 19°C average - Qatar sunshine, avoid summer heat.
Best dates to fly:
Mar 16 - Mar 21 | $690 | 5 days
Mar 16 - Mar 23 | $690 | 7 days
Mar 16 - Mar 26 | $690 | 10 days
That is all for free Economy deals this week. There are 28 premium cabin deals waiting below the paywall - Business Class to Rome at $2,509, Paris at $3,517, Tokyo at $3,234, Dubai at $4,418, and many more. Upgrade to see them all.
💼 Business Class and First Class Deals
This week's premium cabin deals are exceptional. We have Business Class fares to Europe, the Middle East, Asia, and the Caribbean - many of which are 30% to 68% below what you would normally pay. Here are the highlights.
🇪🇺 Business Class - Europe
ORD - Rome (Business Class) - $2,509 round-trip - Multiple Airlines. Mar 31 - Apr 3 (3 nights). Direct. 68% below typical ($2,509-$13,184). Saving over $5,300 vs normal pricing. Midweek departure.
Best dates to fly:
Mar 31 - Apr 3 | $2,509 | 3 days
Mar 31 - Apr 4 | $2,509 | 4 days
Mar 31 - Apr 5 | $2,509 | 5 days
ORD - Lisbon (Business Class) - $2,929 round-trip - Multiple Airlines. Mar 8 - Mar 11 (3 nights). Direct. 40% below typical ($2,929-$6,805). Next week - a premium long weekend in Lisbon.
Best dates to fly:
Mar 8 - Mar 11 | $2,929 | 3 days
Mar 8 - Mar 12 | $2,929 | 4 days
Mar 8 - Mar 13 | $2,929 | 5 days
ORD - Amsterdam (Business Class) - $3,366 round-trip - Multiple Airlines. May 27 - May 30 (3 nights). Direct. 31% below typical ($3,366-$6,384). Near Memorial Day weekend - a premium European escape for the long weekend.
Best dates to fly:
May 27 - May 30 | $3,366 | 3 days
May 27 - May 31 | $3,366 | 4 days
May 27 - Jun 1 | $3,366 | 5 days
ORD - Dublin (Business Class) - $3,414 round-trip - Multiple Airlines. Apr 8 - Apr 11 (3 nights). Direct. 29% below typical ($3,414-$6,255).
Best dates to fly:
Apr 8 - Apr 11 | $3,414 | 3 days
Apr 8 - Apr 12 | $3,414 | 4 days
Apr 8 - Apr 13 | $3,414 | 5 days
ORD - Paris (Business Class) - $3,517 round-trip - Multiple Airlines. Apr 21 - Apr 24 (3 nights). Direct. 38% below typical ($3,517-$7,844). Saving over $2,100 vs normal pricing.
Best dates to fly:
Apr 21 - Apr 24 | $3,517 | 3 days
Apr 21 - Apr 25 | $3,517 | 4 days
Apr 21 - Apr 26 | $3,517 | 5 days
🌏 Business Class - Asia-Pacific
ORD - Delhi (Business Class) - $3,152 round-trip - Multiple Airlines. Mar 16 - Mar 21 (5 nights). Direct. 37% below typical ($3,152-$6,852). Saving $1,850 vs normal pricing. In 2 weeks.
Best dates to fly:
Mar 16 - Mar 21 | $3,152 | 5 days
Mar 16 - Mar 23 | $3,152 | 7 days
Mar 16 - Mar 26 | $3,152 | 10 days
ORD - Tokyo Narita (Business Class) - $3,234 round-trip - Multiple Airlines. Apr 27 - May 2 (5 nights). Direct. 35% below typical ($3,234-$6,693). Saving $1,730 vs normal pricing.
Best dates to fly:
Apr 27 - May 2 | $3,234 | 5 days
Apr 27 - May 4 | $3,234 | 7 days
Apr 27 - May 7 | $3,234 | 10 days
ORD - Tokyo Haneda (Business Class) - $3,234 round-trip - Multiple Airlines. Apr 27 - May 2 (5 nights). Direct. 16% below typical ($3,234-$4,459). Same dates as Narita - compare both airports for availability.
Best dates to fly:
Apr 27 - May 2 | $3,234 | 5 days
Apr 27 - May 4 | $3,234 | 7 days
Apr 27 - May 7 | $3,234 | 10 days
ORD - Hong Kong (Business Class) - $4,163 round-trip - Multiple Airlines. Mar 16 - Mar 21 (5 nights). Direct. 22% below typical ($4,163-$6,491). 17°C - best in cooler months. In 2 weeks.
Best dates to fly:
Mar 16 - Mar 21 | $4,163 | 5 days
Mar 16 - Mar 23 | $4,163 | 7 days
Mar 16 - Mar 26 | $4,163 | 10 days
ORD - Seoul (Business Class) - $4,470 round-trip - Multiple Airlines. Mar 26 - Mar 31 (5 nights). Direct. 15% below typical ($4,470-$6,095). Also note the Seoul Economy deal at $915 - 46% below typical - if you prefer to save and fly Economy.
Best dates to fly:
Mar 26 - Mar 31 | $4,470 | 5 days
Mar 26 - Apr 2 | $4,470 | 7 days
Mar 26 - Apr 5 | $4,470 | 10 days
🕌 Business Class - Middle East
ORD - Dubai (Business Class) - $4,418 round-trip - Multiple Airlines. Mar 16 - Mar 21 (5 nights). Direct. 67% below typical ($4,418-$22,002). Saving over $8,700. This is a genuinely extraordinary discount.
Best dates to fly:
Mar 16 - Mar 21 | $4,418 | 5 days
Mar 16 - Mar 23 | $4,418 | 7 days
Mar 16 - Mar 26 | $4,418 | 10 days
ORD - Tel Aviv (Business Class) - $4,484 round-trip - Multiple Airlines. Mar 16 - Mar 21 (5 nights). Direct. 54% below typical ($4,484-$14,934). Saving over $5,200 vs normal pricing.
Best dates to fly:
Mar 16 - Mar 21 | $4,484 | 5 days
Mar 16 - Mar 23 | $4,484 | 7 days
Mar 16 - Mar 26 | $4,484 | 10 days
🌴 Business Class - Caribbean and Mexico
ORD - Cancun (Business Class) - $193 round-trip - Multiple Airlines. Apr 15 - Apr 20 (5 nights). Direct. 39% below typical ($193-$439). 25°C average. Business Class to Cancun for under $200 is remarkable.
Best dates to fly:
Apr 15 - Apr 20 | $193 | 5 days
Apr 15 - Apr 22 | $193 | 7 days
Apr 15 - Apr 25 | $193 | 10 days
ORD - San Juan (Business Class) - $208 round-trip - Multiple Airlines. Jun 15 - Jun 20 (5 nights). Direct. 28% below typical ($208-$368).
Best dates to fly:
Jun 15 - Jun 20 | $208 | 5 days
Jun 15 - Jun 22 | $208 | 7 days
Jun 15 - Jun 25 | $208 | 10 days
ORD - Punta Cana (Business Class) - $247 round-trip - Multiple Airlines. Apr 13 - Apr 18 (5 nights). Direct. 47% below typical ($247-$688). 26°C average. Dominican Republic beach resorts in Business Class for under $250.
Best dates to fly:
Apr 13 - Apr 18 | $247 | 5 days
Apr 13 - Apr 20 | $247 | 7 days
Apr 13 - Apr 23 | $247 | 10 days
ORD - Montego Bay (Business Class) - $418 round-trip - Multiple Airlines. Mar 24 - Mar 29 (5 nights). Direct. 52% below typical ($418-$1,340). 27°C average. Jamaica Business Class for under $420 - move fast, this is in 3-4 weeks.
Best dates to fly:
Mar 24 - Mar 29 | $418 | 5 days
Mar 24 - Mar 31 | $418 | 7 days
Mar 24 - Apr 3 | $418 | 10 days
🇺🇸 Business Class - Domestic and Canada
ORD - Miami (Business Class) - $127 round-trip - Multiple Airlines. Apr 20 - Apr 25 (5 nights). Direct. 57% below typical ($127-$465).
MDW - Phoenix (Business Class) - $127 round-trip - Multiple Airlines. Apr 24 - Apr 29 (5 nights). Direct. 28% below typical ($127-$228). Midway Business Class to Phoenix - a steal.
ORD - Los Angeles (Business Class) - $160 round-trip - Multiple Airlines. Apr 15 - Apr 20 (5 nights). Direct. 25% below typical ($160-$267).
ORD - Seattle (Business Class) - $274 round-trip - Multiple Airlines. Mar 31 - Apr 5 (5 nights). Direct. 12% below typical ($274-$347).
ORD - San Francisco (Business Class) - $388 round-trip - Multiple Airlines. Mar 24 - Mar 29 (5 nights). Direct. 31% below typical ($388-$740).
ORD - Toronto (Business Class) - $192 round-trip - Multiple Airlines. Mar 28 - Apr 2 (5 nights). Direct. 38% below typical ($192-$424). Weekend departure.
✈️ Chicago Airport Strategies for Premium Travelers
For premium cabin travelers this week, O'Hare (ORD) is the clear winner. All Business Class deals to Europe, Asia, and the Middle East depart exclusively from ORD. Midway (MDW) offers two notable Business Class deals - Phoenix and will have you connecting through fewer terminals than ORD for that specific route.
Europe Business Class - Always use O'Hare (ORD). Better connections and more carrier options.
Caribbean Business Class - O'Hare for Cancun, Punta Cana, Montego Bay, San Juan. All direct.
Domestic Business Class - Both airports work. MDW is more convenient for south and west Chicago suburbs.
Asia and Middle East Business Class - O'Hare only. The hub for long-haul premium travel from Chicago.
Transit tip for ORD: Terminal 1 (United) and Terminal 3 (American) are connected airside. Budget extra time if connecting between terminals 1, 2, and 3.
Want to turn these Business Class fares into award redemptions or stack miles on top of paid bookings? Award Travel Finder tracks the best award flight redemptions daily and often surfaces the exact same routes we feature here - sometimes for 40,000 to 80,000 miles in Business Class. Well worth checking before you book cash.
That is a wrap for this week's Chicago Flight Deals newsletter. We will be back next week with fresh deals from ORD and MDW. In the meantime, if you want daily updates on miles, points, and credit card bonuses to help fund future trips, check out Miles and Points Daily - it is free and publishes every day.
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