* This is a “fare dump” with a few alternate dates available.
MDW > Denver, Colorado: Biz from $506 Econ from $58. – Feb-Apr
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Oakland, California: Econ from $109. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Dallas, Texas: Biz from $409 Econ from $93. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Montego Bay, Jamaica: Biz from $973 Econ from $248. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Burbank, California: Econ from $102. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Armenia, Colombia: Econ from $266. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Monterrey, Mexico: Biz from $676 Econ from $231. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Malaga, Spain: Econ from $407. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Budapest, Hungary: Econ from $523. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Barranquilla, Colombia: Biz from $904 Econ from $247. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Hartford, Connecticut: Biz from $564 Econ from $90. – Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Kinshasa, Democratic Republic of the Congo: Econ from $892. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > San Juan, Puerto Rico: Biz from $812 Econ from $146. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Riga, Latvia: Econ from $500. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Auckland, New Zealand: Econ from $869. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Diego, California: Econ from $114. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Guadalajara, Mexico: Biz from $677 Econ from $212. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Minneapolis, Minnesota: Biz from $281 Econ from $91. – Mar-May (Including Spring Break)
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is an airline…
ORD > Salt Lake City, Utah: Econ from $121. – Feb-Apr
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Belgrade, Serbia: Econ from $544. – Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Dublin, Ireland: Biz from $1142 Econ from $366. – Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Wroclaw, Poland: Econ from $533. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Entebbe, Uganda: Econ from $783. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Phoenix, Arizona: Econ from $97. – Feb-Apr (Including Spring Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Belgrade, Serbia: Econ from $544. – Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Sofia, Bulgaria: Econ from $535. – Feb-Apr (Including Spring Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Simpson Bay, St. Maarten: Econ from $247. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charlotte, North Carolina: Biz from $387 Econ from $54. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Madrid, Spain: Econ from $466. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Boise, Idaho: Biz from $638 Econ from $156. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Warsaw, Poland: Econ from $459. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Porto, Portugal: Econ from $475. – Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Durban, South Africa: Econ from $1025. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Seattle, Washington: Biz from $610 Econ from $95. – Feb-Apr (Including Spring Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Savannah, Georgia: Biz from $564 Econ from $96. – Feb-Apr (Including Spring Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Hartford, Connecticut: Biz from $431 Econ from $98. – Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Tirana, Albania: Biz from $2592 Econ from $571. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Pointe La Rue, Seychelles: Econ from $921. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Houston, Texas: Econ from $97. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…