MultiTripScanner / Start cities / Chicago / Under €500

Longest trips in Europe under €500 from Chicago

€500 per person with a cabin bag takes you from Chicago through 5 countries in Europe: 5 flights for €477, the flight over included, starting in the next two months. The first flight is the cheapest fare from Chicago we've seen lately, often with a stop or two; after it, one city per country, 2–4 nights in each and non-stop flights only. Updated every night.

Prices seen, not held: each says how old it is
Each total says what a cabin bag adds
Each flight is its own ticket
Ranked by price alone

We check the onward non-stop fares from each stop, for each number of nights you allow, and string the cheapest we find into a trip through several countries.

ChicagoLondon2nGothenburg4nGdansk4nMilan2nZagreb

5 flights, 5 countries in Europe, 12 nights, 16–30 Nov.

about€477per person, with a cabin bag

€316 without bags, plus €161 in cabin bags · prices seen up to 8 days ago, may be higher now

See the flightsHide the flights

Chicago

United States, Start, Mon 16 Nov
ORD→LHR Mon 16 Nov leaves 18:35 night flightLeaves from O'Hare International Airport, lands at London Heathrow Airport. Non-stop, Iberia, about 8 hours, cabin bag often extra on long-haul fares: we count about €65€243seen 2 days ago Check price
- you leave London from a different airport (STN, Stansted Airport)
- overnight: it lands on Tue 17 Nov, so your nights in London count from then
London

United Kingdom, 2 nights, 17–19 Nov
Britain's capital on the Thames, with free national museums, royal palaces, the Tower, West End theatres, big parks and food from every corner of the world.
Typical November: highs of 12°C, some rain
- Capital
Swap this stop
STN→GOT Thu 19 Nov leaves 06:15, lands 09:05Ryanair, about 2 hours, cabin bag about €24€23 Check price
- Stansted Airport is 50 km from London · Far airports compared
- a price seen 5 days ago: it may be higher now or sold out
Gothenburg

Sweden, 4 nights, 19–23 Nov
Sweden's second city, a laid-back port with canals, the Liseberg amusement park, seafood halls and cafés for fika. Trams and ferries run out to a car-free archipelago of rocky islands.
Typical November: highs of 7°C, some rain
Swap this stop
GOT→GDN Mon 23 Nov leaves 23:40, lands 00:50 the next day late landingRyanair, about 1 hour, cabin bag about €24€19seen 2 days ago Check price
Gdansk

Poland, 4 nights, 24–28 Nov
A Baltic port city with a rebuilt Hanseatic main street, a medieval crane on the waterfront, the shipyard where Solidarity began and sandy beaches in Brzeźno.
Typical November: highs of 7°C, some rain
- Old town
Swap this stop
GDN→MXP Sat 28 Nov leaves 17:30, lands 19:40Lands at Milano Malpensa Airport. Ryanair, about 2 hours, cabin bag about €24€16 Check price
- you leave Milan from a different airport (BGY, Orio al Serio International Airport)
- a price seen 8 days ago: it may be higher now or sold out
Milan

Italy, 2 nights, 28–30 Nov
Italy's fashion and business capital, with a white Gothic cathedral, Leonardo's Last Supper, La Scala opera house and aperitivo in the Navigli canal district.
Typical November: highs of 12°C, wet
Swap this stop
BGY→ZAG Mon 30 Nov leaves 05:55, lands 07:10 early startMalta Air, about 1½ hours, cabin bag about €24€15 Check price
- Orio al Serio International Airport is 46 km from Milan · Far airports compared
- a price seen 4 days ago: it may be higher now or sold out
Zagreb

Croatia, Last stop, Mon 30 Nov
Croatia's capital, with an upper town of old churches and gas street lamps, Austro-Hungarian squares, café terraces and the Medvednica hills for walks.
Typical November: highs of 11°C, some rain
- Capital
- Old town
Swap this stop

We count €65 for the bag on the long flight; check the airline's price.

We check the onward non-stop fares from each stop, for each number of nights you allow, and string the cheapest we find into a trip through several countries.

Trip page

ChicagoLondon2nMemmingen4nTirana3nRimini

4 flights, 4 countries in Europe, 9 nights, 16–26 Nov.

about€435per person, with a cabin bag

€298 without bags, plus €137 in cabin bags · prices seen up to 5 days ago, may be higher now

See the flightsHide the flights

Chicago

United States, Start, Mon 16 Nov
ORD→LHR Mon 16 Nov leaves 18:35 night flightLeaves from O'Hare International Airport, lands at London Heathrow Airport. Non-stop, Iberia, about 8 hours, cabin bag often extra on long-haul fares: we count about €65€243seen 2 days ago Check price
- you leave London from a different airport (STN, Stansted Airport)
- overnight: it lands on Tue 17 Nov, so your nights in London count from then
London

United Kingdom, 2 nights, 17–19 Nov
Britain's capital on the Thames, with free national museums, royal palaces, the Tower, West End theatres, big parks and food from every corner of the world.
Typical November: highs of 12°C, some rain
- Capital
Swap this stop
STN→FMM Thu 19 Nov leaves 07:25, lands 10:05Ryanair, about 1½ hours, cabin bag about €24€20 Check price
- Stansted Airport is 50 km from London · Far airports compared
- a price seen 3 days ago: it may be higher now or sold out
Memmingen

Germany, 4 nights, 19–23 Nov
A small Swabian town with a well-kept old centre in the Allgäu, the gateway to Bavaria's foothills. Neuschwanstein castle, alpine lakes, hiking and ski areas are all within about an hour.
Typical November: highs of 7°C, some rain
- Small town
Swap this stop
FMM→TIA Mon 23 Nov leaves 13:15, lands 15:15Ryanair, about 2 hours, cabin bag about €24€19 Check price
- a price seen 4 days ago: it may be higher now or sold out
Tirana

Albania, 3 nights, 23–26 Nov
Albania's capital, a city of painted blocks, cafés and Communist-era bunkers turned museums, with a cable car up Mount Dajti just outside town.
Typical November: highs of 18°C, wet
- Capital
Swap this stop
TIA→RMI Thu 26 Nov leaves 06:05, lands 07:45Ryanair, about 1½ hours, cabin bag about €24€16 Check price
- a price seen 5 days ago: it may be higher now or sold out
Rimini

Italy, Last stop, Thu 26 Nov
Adriatic resort with miles of beach clubs and nightlife, a Roman arch and bridge in the old centre, and hilltop San Marino close by.
Typical November: highs of 14°C, some rain
- Beach
Swap this stop

We count €65 for the bag on the long flight; check the airline's price.

We check the onward non-stop fares from each stop, for each number of nights you allow, and string the cheapest we find into a trip through several countries.

Trip page

ChicagoLondon2nMemmingen4nTirana

3 flights, 3 countries in Europe, 6 nights, 16–23 Nov.

about€395per person, with a cabin bag

€282 without bags, plus €113 in cabin bags · prices seen up to 4 days ago, may be higher now

See the flightsHide the flights

Chicago

United States, Start, Mon 16 Nov
ORD→LHR Mon 16 Nov leaves 18:35 night flightLeaves from O'Hare International Airport, lands at London Heathrow Airport. Non-stop, Iberia, about 8 hours, cabin bag often extra on long-haul fares: we count about €65€243seen 2 days ago Check price
- you leave London from a different airport (STN, Stansted Airport)
- overnight: it lands on Tue 17 Nov, so your nights in London count from then
London

United Kingdom, 2 nights, 17–19 Nov
Britain's capital on the Thames, with free national museums, royal palaces, the Tower, West End theatres, big parks and food from every corner of the world.
Typical November: highs of 12°C, some rain
- Capital
Swap this stop
STN→FMM Thu 19 Nov leaves 07:25, lands 10:05Ryanair, about 1½ hours, cabin bag about €24€20 Check price
- Stansted Airport is 50 km from London · Far airports compared
- a price seen 3 days ago: it may be higher now or sold out
Memmingen

Germany, 4 nights, 19–23 Nov
A small Swabian town with a well-kept old centre in the Allgäu, the gateway to Bavaria's foothills. Neuschwanstein castle, alpine lakes, hiking and ski areas are all within about an hour.
Typical November: highs of 7°C, some rain
- Small town
Swap this stop
FMM→TIA Mon 23 Nov leaves 13:15, lands 15:15Ryanair, about 2 hours, cabin bag about €24€19 Check price
- a price seen 4 days ago: it may be higher now or sold out
Tirana

Albania, Last stop, Mon 23 Nov
Albania's capital, a city of painted blocks, cafés and Communist-era bunkers turned museums, with a cable car up Mount Dajti just outside town.
Typical November: highs of 18°C, wet
- Capital
Swap this stop

We count €65 for the bag on the long flight; check the airline's price.

We check the onward non-stop fares from each stop, for each number of nights you allow, and string the cheapest we find into a trip through several countries.

Trip page

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Type a city or a country, or pick “Anywhere in Europe” for the cheapest start. From Canada or the US, type your home airport (e.g. Calgary or BOS): trips start with a flight from the nearest of 11 big airports there (Vancouver, Toronto, Montreal and more), and the budget covers it.

Then fly on toFrom Vancouver, Los Angeles or San Francisco, or an airport near them: a few places in Europe, one long flight on to Southeast Asia, a few places there, and home. Three long-haul tickets, all in the budget.

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Prices go up to 12 Feb; later dates are added daily.

Trip2+ places, 2–4 nights each

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EndsAnywhere

Where it endsBack homeAnywhereIn a city

Total for all flightsUp to €500

Budget for all flights Only a small under-seat bag (leaves out the cabin bag)Only trips low for their dates (under what their flights usually cost)Leave it empty for no cap. Back home counts the flight home. With a cabin bag, each flight counts its airline's usual price for one, or €60 where we don't know it (€65 on a long flight).

Travellers1 adult

TravellersEvery price, the budget included, is for all of you.

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Prices are for one traveller, flights with a cabin bag, the cheapest seen lately.