Chicago Flight Deals: Fly to Phoenix for Just $28 Round-Trip This Week

Your weekly roundup of the best flight deals from Chicago's O'Hare (ORD) and Midway (MDW) airports - curated every Thursday so you never miss a bargain. This week we've spotted 57 deals across domestic, Caribbean, European, and Asian routes, with prices starting at an almost unbelievable $28 round-trip. February in Chicago means one thing: it's cold. Really cold. But the good news? Your next escape is cheaper than ever.

Escape the Chicago cold with these warm getaways - all departing from ORD or MDW. While temps in the city hover around -2°C, these destinations are basking in sunshine.

Below you'll find this week's top economy deals grouped by region. All prices are round-trip unless noted. Click any route to search directly on Google Flights.

MDW → Phoenix - $28 round-trip ✅ Good Deal (64% below typical). Multiple Airlines. Apr 19–24 (5 nights, departing Sunday). Direct flight. This is the headline deal of the week - $28 round-trip from Midway to Phoenix is almost unheard of. Act fast.

Best dates to fly:• Apr 19–24 | $28 | 5 days• Apr 19–26 | $28 | 7 days• Apr 19–29 | $28 | 10 days

ORD → Miami - $35 round-trip ✅ Good Deal (48% below typical). Multiple Airlines. Apr 18–23 (5 nights, departing Saturday). Direct flight. 🌴 Warm escape - 21°C at your destination vs -2°C in Chicago.

Best dates to fly:• Apr 18–23 | $35 | 5 days• Apr 18–25 | $35 | 7 days• Apr 18–28 | $35 | 10 days

ORD → Los Angeles - $44 round-trip ✅ Good Deal (52% below typical). Multiple Airlines. Apr 14–19 (5 nights, departing Tuesday - midweek discount). Direct flight.

Best dates to fly:• Apr 14–19 | $44 | 5 days• Apr 14–21 | $44 | 7 days• Apr 14–24 | $44 | 10 days

ORD → San Francisco - $109 round-trip ✅ Good Deal (42% below typical). Multiple Airlines. Mar 12–17 (5 nights, in 3–4 weeks). Direct flight.

Best dates to fly:• Mar 12–17 | $109 | 5 days• Mar 12–19 | $109 | 7 days• Mar 12–22 | $109 | 10 days

ORD → Seattle - $118 round-trip ✅ Good Deal (25% below typical). Multiple Airlines. Mar 17–22 (5 nights, departing Tuesday). Direct flight.

Best dates to fly:• Mar 17–22 | $118 | 5 days• Mar 17–24 | $118 | 7 days• Mar 17–27 | $118 | 10 days

MDW → Las Vegas - $99 round-trip ✅ Good Deal (38% below typical). Multiple Airlines. Apr 14–19 (5 nights, departing Tuesday). Direct flight from Midway - great for a long weekend in Vegas.

Best dates to fly:• Apr 14–19 | $99 | 5 days• Apr 14–21 | $99 | 7 days• Apr 14–24 | $99 | 10 days

ORD → Montego Bay - $118 round-trip ✅ Good Deal (72% below typical - the biggest percentage saving this week!). Multiple Airlines. Mar 17–22 (5 nights, in 3–4 weeks). Direct flight. 🌴 27°C - Jamaica sunshine and reggae vibes await.

Best dates to fly:• Mar 17–22 | $118 | 5 days• Mar 17–24 | $118 | 7 days• Mar 17–27 | $118 | 10 days

ORD → Cancun - $93 round-trip ✅ Good Deal (42% below typical). Multiple Airlines. Apr 13–18 (5 nights, departing Monday). Direct flight. 🌴 25°C - beach paradise with warm Caribbean waters.

Best dates to fly:• Apr 13–18 | $93 | 5 days• Apr 13–20 | $93 | 7 days• Apr 13–23 | $93 | 10 days

ORD → San Juan - $95 round-trip ✅ Good Deal (52% below typical). Multiple Airlines. Mar 16–21 (5 nights, in 3–4 weeks). Direct flight. No passport required for US citizens - warm Caribbean sun included.

Best dates to fly:• Mar 16–21 | $95 | 5 days• Mar 16–23 | $95 | 7 days• Mar 16–26 | $95 | 10 days

ORD → Punta Cana - $103 round-trip ✅ Good Deal (51% below typical). Multiple Airlines. Apr 11–16 (5 nights, departing Saturday - perfect weekend start). Direct flight. 🌴 26°C - Dominican Republic beach resorts.

Best dates to fly:• Apr 11–16 | $103 | 5 days• Apr 11–18 | $103 | 7 days• Apr 11–21 | $103 | 10 days

Pro tip: These Caribbean routes fly out of O'Hare (ORD), which has the widest range of direct Caribbean connections from Chicago. If you're chasing warm weather deals and want to earn miles while doing it, Miles & Points Daily covers the best credit card sign-up bonuses daily - a great way to offset the cost of your next tropical escape.

Europe is wide open this late winter and spring - with prices from ORD starting under $400 to major cities including Paris, London, Rome, and Madrid. These deals are available next week, so if Europe is calling, move fast.

ORD → Paris - $394 round-trip ✅ Good Deal (58% below typical). Multiple Airlines. Mar 1–4 (3 nights - next week!). Direct flight. A quick long-weekend Paris getaway at an exceptional price.

Best dates to fly:• Mar 1–4 | $394 | 3 days• Mar 1–5 | $394 | 4 days• Mar 1–6 | $394 | 5 days

ORD → London Heathrow - $399 round-trip ✅ Good Deal (38% below typical). Multiple Airlines. Mar 1–4 (3 nights - next week, departing Sunday). Direct flight.

Best dates to fly:• Mar 1–4 | $399 | 3 days• Mar 1–5 | $399 | 4 days• Mar 1–6 | $399 | 5 days

ORD → Rome - $399 round-trip ✅ Good Deal (57% below typical). Multiple Airlines. Mar 1–4 (3 nights - next week, departing Sunday). Direct flight. Incredible value for the Eternal City.

Best dates to fly:• Mar 1–4 | $399 | 3 days• Mar 1–5 | $399 | 4 days• Mar 1–6 | $399 | 5 days

ORD → Dublin - $414 round-trip ✅ Good Deal (65% below typical). Multiple Airlines. Feb 26–Mar 1 (3 nights - this is next week, departing Thursday!). Direct flight. One of the biggest savings percentages in the Europe section.

Best dates to fly:• Feb 26–Mar 1 | $414 | 3 days• Feb 26–Mar 2 | $414 | 4 days• Feb 26–Mar 3 | $414 | 5 days

ORD → Madrid - $415 round-trip ✅ Good Deal (76% below typical - the biggest savings percentage in Europe this week). Multiple Airlines. Mar 1–4 (3 nights - next week, departing Sunday). Direct flight.

Best dates to fly:• Mar 1–4 | $415 | 3 days• Mar 1–5 | $415 | 4 days• Mar 1–6 | $415 | 5 days

ORD → Lisbon - $418 round-trip ✅ Good Deal (57% below typical). Multiple Airlines. Mar 1–4 (3 nights - next week, departing Sunday). Direct flight. Lisbon has mild 13°C weather - much warmer than Chicago!

Best dates to fly:• Mar 1–4 | $418 | 3 days• Mar 1–5 | $418 | 4 days• Mar 1–6 | $418 | 5 days

ORD → Amsterdam - $395 round-trip ✅ Good Deal (27% below typical). Multiple Airlines. Apr 20–23 (3 nights, departing Monday). Direct flight. Spring tulip season in Amsterdam - a stunning time to visit.

Best dates to fly:• Apr 20–23 | $395 | 3 days• Apr 20–24 | $395 | 4 days• Apr 20–25 | $395 | 5 days

ORD → Barcelona - $419 round-trip ✅ Good Deal (29% below typical). Multiple Airlines. Apr 15–18 (3 nights, departing Wednesday). Direct flight. Mediterranean beaches and culture - a perfect spring city break.

Best dates to fly:• Apr 15–18 | $419 | 3 days• Apr 15–19 | $419 | 4 days• Apr 15–20 | $419 | 5 days

Heads up for points fans: Several of these European routes could also be booked with airline miles. Award Travel Finder tracks the best award flight redemptions daily - check there if you'd rather use points than cash for your ORD → Europe trip.

ORD → Delhi - $290 round-trip ✅ Good Deal (43% below typical). Multiple Airlines. Mar 9–14 (5 nights, in 2 weeks - departing Monday). Direct flight. 17°C in Delhi right now - the best time of year to visit before the summer heat.

Best dates to fly:• Mar 9–14 | $290 | 5 days• Mar 9–16 | $290 | 7 days• Mar 9–19 | $290 | 10 days

ORD → Hong Kong - $535 round-trip ✅ Good Deal (51% below typical). Multiple Airlines. Mar 5–10 (5 nights, in 2 weeks, departing Thursday). Direct flight. 17°C - best in cooler months. An exceptional long-haul price from ORD.

Best dates to fly:• Mar 5–10 | $535 | 5 days• Mar 5–12 | $535 | 7 days• Mar 5–15 | $535 | 10 days

ORD → Tokyo Haneda - $594 round-trip ✅ Good Deal (32% below typical). Multiple Airlines. Apr 7–12 (5 nights, departing Tuesday). Direct flight. Spring in Tokyo - cherry blossom season at an outstanding price.

Best dates to fly:• Apr 7–12 | $594 | 5 days• Apr 7–14 | $594 | 7 days• Apr 7–17 | $594 | 10 days

ORD → Tokyo Narita - $594 round-trip ✅ Good Deal (24% below typical). Multiple Airlines. Apr 12–17 (5 nights, departing Sunday). Direct flight. Two Tokyo airport options this week - both at the same price. Choose based on your hotel location.

Best dates to fly:• Apr 12–17 | $594 | 5 days• Apr 12–19 | $594 | 7 days• Apr 12–22 | $594 | 10 days

ORD → Toronto - $85 round-trip ✅ Good Deal (55% below typical). Multiple Airlines. Mar 12–17 (5 nights, in 3–4 weeks, departing Thursday). Direct flight. A quick and cheap hop across the border - great for a food and culture weekend.

Best dates to fly:• Mar 12–17 | $85 | 5 days• Mar 12–19 | $85 | 7 days• Mar 12–22 | $85 | 10 days

This week's premium cabin deals from Chicago are exceptional - with Business Class prices on some routes at 50–68% below typical fares. Here are the standout deals for premium subscribers.

MDW → Phoenix (Business) - $127 round-trip (44% below typical, usually $127–$328). Apr 19–24. Direct. Business Class from Midway to Phoenix for $127 - an absurd price for a premium cabin on a domestic route.

Best dates:• Apr 19–24 | $127 | 5 days• Apr 19–26 | $127 | 7 days• Apr 19–29 | $127 | 10 days

ORD → Miami (Business) - $134 round-trip (45% below typical, usually $134–$350). Apr 18–23. Direct. Business Class to Miami in April - warm weather, beach access, and an upgraded cabin for under $135.

Best dates:• Apr 18–23 | $134 | 5 days• Apr 18–25 | $134 | 7 days• Apr 18–28 | $134 | 10 days

ORD → Los Angeles (Business) - $153 round-trip (33% below typical, usually $153–$304). Apr 14–19. Direct. Business Class to LA for the price of a cheap economy ticket on many routes.

ORD → Seattle (Business) - $271 round-trip (12% below typical, usually $271–$344). Apr 2–7. Direct. A solid Business Class deal to Seattle for a spring city break.

ORD → Cancun (Business) - $192 round-trip (32% below typical, usually $192–$376). Apr 14–19. Direct. 🌴 25°C - Business Class to Cancun's Caribbean beaches for under $200. This is a standout deal.

ORD → Punta Cana (Business) - $243 round-trip (48% below typical, usually $243–$686). Apr 12–17. Direct. 🌴 26°C - Dominican Republic resort Business Class at nearly half price.

ORD → San Juan (Business) - $239 round-trip (30% below typical, usually $233–$454). Jun 1–6. Direct. A summer Business Class deal around Memorial Day weekend - book early.

ORD → Montego Bay (Business) - $428 round-trip (29% below typical, usually $428–$771). Apr 5–10. Direct. 🌴 27°C - Jamaica in Business Class for spring break season.

ORD → Rome (Business) - $2,509 round-trip (68% below typical, usually $2,509–$13,384 - saving up to $10,875!). Mar 3–6. Direct. The biggest Business Class saving in Europe this week. Typical prices for this route go above $13,000 - this is exceptional.

Best dates:• Mar 3–6 | $2,509 | 3 days• Mar 3–7 | $2,509 | 4 days• Mar 3–8 | $2,509 | 5 days

ORD → Dublin (Business) - $3,449 round-trip (45% below typical, usually $3,449–$9,196). Mar 24–27. Direct. Business Class to Dublin - 45% off with prices up to $9,196 typically on this route.

ORD → Lisbon (Business) - $2,929 round-trip (40% below typical, usually $2,929–$6,805). Feb 27–Mar 2. Direct. A rare last-minute Business Class deal to Lisbon - departing this Friday!

ORD → Amsterdam (Business) - $3,316 round-trip (31% below typical, usually $3,316–$6,334). May 20–23. Direct. Plan ahead for a Memorial Day Business Class escape to Amsterdam.

ORD → Paris (Business) - $3,467 round-trip (8% below typical, usually $3,467–$4,067). Apr 14–17. Direct. Paris Business Class in spring - a smaller discount but typical prices can reach $13,000+ on flexible dates.

ORD → Delhi (Business) - $3,152 round-trip (50% below typical, usually $3,152–$9,477 - saving up to $6,325). Mar 9–14. Direct. Half-price Business Class to India - in 2 weeks. A remarkable deal if you can move fast.

Best dates:• Mar 9–14 | $3,152 | 5 days• Mar 9–16 | $3,152 | 7 days• Mar 9–19 | $3,152 | 10 days

ORD → Tokyo Narita (Business) - $3,234 round-trip (19% below typical, usually $3,234–$4,729 - flexible dates can reach $17,535!). Apr 23–28. Direct. Business Class to Tokyo Narita - cherry blossom season wrapping up, golden week beginning.

ORD → Tokyo Haneda (Business) - $3,234 round-trip (16% below typical, usually $3,234–$4,459). Apr 23–28. Direct. Same price as Narita - Haneda is the better choice for staying in central Tokyo.

ORD → Hong Kong (Business) - $4,163 round-trip (22% below typical, usually $4,163–$6,491). Mar 9–14. Direct. Business Class to Hong Kong - 22% off with savings of over $1,100.

ORD → Seoul (Business) - $4,470 round-trip (15% below typical, usually $4,470–$6,095). Mar 19–24. Direct. Business Class to Seoul in spring - K-culture, food, and cherry blossoms.

ORD → Dubai (Business) - $4,418 round-trip (56% below typical, usually $4,418–$15,504 - saving up to $11,086!). Mar 9–14. Direct. 🌴 20°C - desert luxury and Business Class at 56% off is one of the most extraordinary deals in this week's premium section.

Best dates:• Mar 9–14 | $4,418 | 5 days• Mar 9–16 | $4,418 | 7 days• Mar 9–19 | $4,418 | 10 days

ORD → Tel Aviv (Business) - $4,484 round-trip (20% below typical, usually $4,484–$6,734). Mar 5–10. Direct. Business Class to Tel Aviv - departing in 2 weeks.

ORD → Toronto (Business) - $192 round-trip (37% below typical, usually $192–$419). Mar 15–20. Direct. Weekend Business Class to Toronto for under $200 - departs Sunday, returns Friday.

Best dates:• Mar 15–20 | $192 | 5 days• Mar 15–22 | $192 | 7 days• Mar 15–25 | $192 | 10 days

Not all Chicago airport deals are created equal. Here's how to choose between O'Hare and Midway based on where you're going.

Want to go deeper on earning miles for these routes? Miles & Points Daily breaks down the best credit card bonuses and earning strategies every day - ideal for frequent travelers departing from ORD and MDW who want to maximize every dollar spent on flights.

That's it for this week's Chicago Flight Deals. Deals move fast - especially that $28 Phoenix and the next-week Europe fares. Happy travels, Chicago. ✈️

Award Travel Finder hunts down the best redemptions so you don't have to.

See all deals at AwardTravelFinder.com →