Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Piarco, Trinidad and Tobago: Biz from $860 Econ from $308. – May-Jul (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cartagena, Colombia: Biz from $671 Econ from $293.- Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Pedro Sula, Honduras: Biz from $725 Econ from $293.- Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Minneapolis, Minnesota: Biz from $261 Econ from $107.- Feb-Apr (Including Spring Break)
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
ORD > Addis Ababa, Ethiopia: Econ from $943.- Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Pedro Sula, Honduras: Biz from $582 Econ from $264.- Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Miami, Florida: Biz from $212 Econ from $50.- Feb-Apr (Including Spring Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > San Diego, California: Econ from $117.- Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Oranjestad, Aruba: Biz from $531 Econ from $218.- Feb-Apr
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > Mexico City, Mexico: Biz from $680 Econ from $208.- Feb-Apr
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Boston, Massachusetts: Biz from $286 Econ from $104.- Feb-Apr (Including Spring Break)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Guayaquil, Ecuador: Biz from $613 Econ from $265.- Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Pedro Sula, Honduras: Biz from $720 Econ from $263.- Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Montego Bay, Jamaica: Biz from $543 Econ from $267.- Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Liberia, Costa Rica: Biz from $1166 Econ from $341. – Mar-May (Including Spring Break)
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
MDW > San Juan, Puerto Rico: Biz from $406 Econ from $178. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Belize City, Belize: Biz from $859 Econ from $321. – Feb-Apr
* This is a “fare dump” with a few alternate dates available.
MDW > Knoxville, Tennessee: Econ from $167. – Jun-Aug (Including Fourth of July and Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Montego Bay, Jamaica: Biz from $531 Econ from $278.- Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Juan, Puerto Rico: Econ from $176.- Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kingston, Jamaica: Biz from $650 Econ from $337.- Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Asheville, North Carolina: Econ from $166.- Dec-Feb [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > San Diego, California: Econ from $151.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Montego Bay, Jamaica: Biz from $513 Econ from $276.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cartagena, Colombia: Biz from $625 Econ from $247. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Leon, Mexico: Biz from $652. Econ from $264. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Diego, California: Econ from $122.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Belize City, Belize: Biz from $640. Econ from $303. – Dec-Feb [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Cozumel, Mexico: Biz from $1003 Econ from $246.- Feb-Apr
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Colombo, Sri Lanka: Econ from $735. – Mar-May (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 > Montego Bay, Jamaica: Biz from $566 Econ from $299.- Nov-Jan (Including Winter Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Prague, Czech Republic: Econ from $447. – Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Bangkok, Thailand: Econ from $682. – Jan-Mar [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Coxen Hole, Honduras: Biz from $1424. Econ from $489. – Nov-Jan
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
ORD > Thera, Greece: Econ from $674. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubai, United Arab Emirates: Econ from $589. – 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 > Hamburg, Germany: Econ from $515. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > George Town, Cayman Islands: Biz from $660 Econ from $305. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Belgrade, Serbia: Econ from $485. – 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…