Where can I go for $5,000 from Chicago?

1219 destinations fit a $5,000 budget for 2 travellers over 7 days — and that's the whole trip: flights, lodging, food, getting around, things to do, transfers and insurance.

San Jose

Costa Rica

$4,851

likely $4,269–$5,433 · $2,426/person

Premium 6h flight

Flights $722 Lodging $1,173 Food $1,190 Getting around $532

likely $4,263–$5,426 · $2,422/person

Premium 9h flight

Flights $1,612 Lodging $790 Food $840 Getting around $350

likely $4,200–$5,346 · $2,386/person

Premium 11h flight

Flights $1,492 Lodging $969 Food $1,120 Getting around $364

likely $4,180–$5,320 · $2,375/person

Premium Good time to go 17h flight

Flights $2,122 Lodging $874 Food $700 Getting around $350

likely $4,100–$5,218 · $2,330/person

Premium 4h flight

Flights $508 Lodging $1,377 Food $1,190 Getting around $490

likely $4,070–$5,180 · $2,312/person

Premium Good time to go 18h flight

Flights $2,152 Lodging $773 Food $700 Getting around $308

likely $4,019–$5,116 · $2,284/person

Premium 19h flight

Flights $2,218 Lodging $638 Food $700 Getting around $336

likely $3,563–$4,535 · $2,024/person

Premium Good time to go 5h flight

Flights $544 Lodging $1,277 Food $980 Getting around $392

likely $3,249–$4,136 · $1,846/person

Premium 7h flight

Flights $954 Lodging $790 Food $812 Getting around $350

likely $4,250–$5,409 · $2,415/person

Comfortable 9h flight

Flights $1,234 Lodging $1,148 Food $1,190 Getting around $350

$170 left over

Singapore

$4,785

likely $4,211–$5,359 · $2,392/person

Comfortable 20h flight

Flights $2,334 Lodging $867 Food $700 Getting around $210

likely $4,182–$5,323 · $2,376/person

Comfortable Good time to go 14h flight

Flights $1,958 Lodging $974 Food $812 Getting around $280

likely $4,123–$5,248 · $2,343/person

Comfortable Good time to go 19h flight

Flights $2,494 Lodging $706 Food $560 Getting around $252

likely $4,066–$5,174 · $2,310/person

Comfortable 10h flight

Flights $1,276 Lodging $1,020 Food $1,190 Getting around $280

likely $4,034–$5,135 · $2,292/person

Comfortable 10h flight

Flights $1,268 Lodging $1,096 Food $1,120 Getting around $280

likely $3,932–$5,004 · $2,234/person

Comfortable Good time to go 14h flight

Flights $1,996 Lodging $840 Food $728 Getting around $252

likely $3,849–$4,899 · $2,187/person

Comfortable 9h flight

Flights $1,176 Lodging $1,020 Food $1,120 Getting around $294

likely $3,773–$4,802 · $2,144/person

Comfortable 11h flight

Flights $1,442 Lodging $842 Food $980 Getting around $252

likely $3,669–$4,670 · $2,085/person

Comfortable 15h flight

Flights $2,004 Lodging $638 Food $700 Getting around $224

likely $3,603–$4,585 · $2,047/person

Comfortable 11h flight

Flights $1,414 Lodging $816 Food $924 Getting around $252

likely $3,486–$4,436 · $1,980/person

Comfortable 10h flight

Flights $1,340 Lodging $765 Food $910 Getting around $252

likely $3,467–$4,413 · $1,970/person

Comfortable 21h flight

Flights $2,402 Lodging $408 Food $420 Getting around $196

likely $3,421–$4,353 · $1,944/person

Comfortable 10h flight

Flights $1,342 Lodging $765 Food $868 Getting around $252

likely $3,382–$4,305 · $1,922/person

Comfortable Good time to go 13h flight

Flights $2,094 Lodging $591 Food $476 Getting around $154

likely $3,351–$4,265 · $1,904/person

Comfortable 12h flight

Flights $1,586 Lodging $612 Food $756 Getting around $210

likely $3,265–$4,156 · $1,855/person

Comfortable Good time to go 19h flight

Flights $2,200 Lodging $470 Food $420 Getting around $168

likely $3,238–$4,120 · $1,840/person

Comfortable 10h flight

Flights $1,286 Lodging $663 Food $840 Getting around $238

likely $3,054–$3,887 · $1,735/person

Comfortable Good time to go 10h flight

Flights $1,646 Lodging $605 Food $504 Getting around $168

likely $3,047–$3,877 · $1,731/person

Comfortable 9h flight

Flights $1,246 Lodging $612 Food $770 Getting around $210

likely $3,009–$3,829 · $1,710/person

Comfortable 11h flight

Flights $1,440 Lodging $561 Food $672 Getting around $182

likely $2,998–$3,815 · $1,703/person

Comfortable 12h flight

Flights $1,666 Lodging $484 Food $560 Getting around $168

likely $2,991–$3,807 · $1,700/person

Comfortable Good time to go 3h flight

Flights $446 Lodging $1,075 Food $924 Getting around $280

likely $2,959–$3,765 · $1,681/person

Comfortable 11h flight

Flights $1,518 Lodging $510 Food $630 Getting around $168

likely $2,907–$3,700 · $1,652/person

Comfortable Good time to go 5h flight

Flights $516 Lodging $907 Food $812 Getting around $336

likely $2,904–$3,696 · $1,650/person

Comfortable 6h flight

Flights $718 Lodging $816 Food $770 Getting around $280

likely $2,900–$3,690 · $1,648/person

Comfortable 9h flight

Flights $1,234 Lodging $561 Food $728 Getting around $196

likely $2,553–$3,249 · $1,450/person

Comfortable 5h flight

Flights $696 Lodging $663 Food $630 Getting around $252

likely $3,778–$4,808 · $2,147/person

Lean Good time to go 20h flight

Flights $2,524 Lodging $571 Food $560 Getting around $154

likely $3,247–$4,133 · $1,845/person

Lean 10h flight

Flights $1,346 Lodging $714 Food $840 Getting around $196

likely $3,223–$4,101 · $1,831/person

Lean Good time to go 16h flight

Flights $2,016 Lodging $504 Food $490 Getting around $140

likely $2,903–$3,695 · $1,650/person

Lean 10h flight

Flights $1,298 Lodging $663 Food $630 Getting around $196

likely $2,768–$3,524 · $1,573/person

Lean 7h flight

Flights $898 Lodging $612 Food $770 Getting around $210

likely $3,943–$5,914 · $2,464/person

Premium Good time to go 19h flight

Flights $2,198 Lodging $806 Food $672 Getting around $350

likely $3,914–$5,871 · $2,446/person

Premium 19h flight

Flights $2,266 Lodging $688 Food $700 Getting around $364

likely $3,912–$5,868 · $2,445/person

Premium 20h flight

Flights $2,324 Lodging $714 Food $770 Getting around $350

likely $3,884–$5,826 · $2,427/person

Premium Good time to go 9h flight

Flights $1,566 Lodging $1,129 Food $910 Getting around $378

likely $3,796–$5,695 · $2,373/person

Premium 18h flight

Flights $2,140 Lodging $740 Food $770 Getting around $364

likely $3,787–$5,681 · $2,367/person

Premium 12h flight

Flights $1,616 Lodging $918 Food $1,064 Getting around $350

$266 left over

Showing 48 of 1219. See them all →

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$5,000 from somewhere else

Atlanta Boston Charlotte Dallas Denver Detroit Houston Los Angeles Miami Minneapolis New York Newark

Why the whole trip and not just the flight? A cheap flight is a terrible predictor of a cheap trip. From New York in May, Reykjavik has the cheapest airfare of a typical shortlist at about $836 — but the trip runs near $5,600, almost seven times the fare. Hanoi has the most expensive flight at roughly $2,450 and a trip around $3,800. Pricing airfare alone points you at the wrong places.

Run your own numbers →