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Two weeks in Europe from Chicago, there and back

€797 per person with a cabin bag buys two weeks in Europe from Chicago, the flights over and home included: through 3 countries, out on Fri 27 Nov, back on Fri 11 Dec. Each trip below leaves Chicago in the next month and is back there exactly 14 days later. The flights over and home are the cheapest fares from Chicago we've seen lately, often with a stop or two; in between, one city per country, 2–5 nights in each and non-stop flights only. Updated every night.

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.

ChicagoLondon5nMadrid3nLisbon5nChicago

4 flights, 3 countries in Europe, 13 nights, 27 Nov – 11 Dec.

All three places are capitals. Typical November and December highs run from 10°C in Madrid to 15°C in Lisbon.

about€797per person, with a cabin bag

€643 without bags, plus €154 in cabin bags · prices seen up to 6 days ago, may be higher now

See the flightsHide the flights

  1. Chicago

    United States, Start, Fri 27 Nov

  2. ORD→LHR Fri 27 Nov leaves 11:00Leaves from O'Hare International Airport, lands at London Heathrow Airport. 1 stop, JetBlue first, check the travel time and bag rules€269 Check price
    • you leave London from a different airport (STN, Stansted Airport)
    • a price seen 6 days ago: it may be higher now or sold out
    • overnight: it lands on Sat 28 Nov, so your nights in London count from then

  3. London

    United Kingdom, 5 nights, 28 Nov – 3 Dec

    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

  4. STN→MAD Thu 3 Dec leaves 06:15, lands 09:45Ryanair, about 2½ hours, cabin bag about €24€18seen yesterday Check price

  5. Madrid

    Spain, 3 nights, 3–6 Dec

    Spain's capital on the high central plateau, with the Prado and Reina Sofía museums, the Retiro park, late-night tapas and the Guadarrama mountains an hour north.

    Typical December: highs of 10°C, some rain
    • Capital
    • Old town
    • Ski

    Swap this stop

  6. MAD→LIS Sun 6 Dec leaves 14:55, lands 15:20TAP Air Portugal, about 1½ hours, cabin bag usually included€35seen 2 days ago Check price

  7. Lisbon

    Portugal, 5 nights, 6–11 Dec

    Portugal's capital, on hills above the Tagus, with old trams, tiled facades, fado bars in Alfama, the monastery at Belém and Atlantic beaches a short ride away.

    Typical December: highs of 15°C, wet
    • Capital
    • Old town

    Swap this stop

  8. LIS→ORD Fri 11 Dec leaves 11:55Lands at O'Hare International Airport. Non-stop, TAP Air Portugal, about 9½ hours, cabin bag often extra on long-haul fares: we count about €65€321 Check price
    • a price seen 3 days ago: it may be higher now or sold out

  9. Chicago

    United States, Home, Fri 11 Dec

We count up to €65 a bag on each of the 2 long flights; check the airlines' prices.

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.

Open this tripSeparate tickets: if one flight is late or cancelled, the next airline won't wait.
Trip page

ChicagoLondon5nMilan5nBarcelona3nChicago

4 flights, 3 countries in Europe, 13 nights, 26 Nov – 10 Dec.

London is a capital and Barcelona is on the coast. Typical November and December highs run from 7°C in Milan to 15°C in Barcelona.

about€809per person, with a cabin bag

€631 without bags, plus €178 in cabin bags · prices seen up to 5 days ago, may be higher now

See the flightsHide the flights

  1. Chicago

    United States, Start, Thu 26 Nov

  2. ORD→LHR Thu 26 Nov leaves 11:00Leaves from O'Hare International Airport, lands at London Heathrow Airport. 1 stop, JetBlue first, check the travel time and bag rules€270 Check price
    • you leave London from a different airport (STN, Stansted Airport)
    • a price seen 5 days ago: it may be higher now or sold out
    • overnight: it lands on Fri 27 Nov, so your nights in London count from then

  3. London

    United Kingdom, 5 nights, 27 Nov – 2 Dec

    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

  4. STN→BGY Wed 2 Dec leaves 07:45, lands 10:40Ryanair, about 2 hours, cabin bag about €24€20 Check price

  5. Milan

    Italy, 5 nights, 2–7 Dec

    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 December: highs of 7°C, some rain

    Swap this stop

  6. BGY→BCN Mon 7 Dec leaves 05:45, lands 07:20 early startMalta Air, about 1½ hours, cabin bag about €24€23 Check price
    • Orio al Serio International Airport is 46 km from Milan · Far airports compared
    • a price seen 3 days ago: it may be higher now or sold out

  7. Barcelona

    Spain, 3 nights, 7–10 Dec

    Catalonia's capital on the Mediterranean, known for Gaudí's Sagrada Família and Park Güell, the Gothic Quarter, city beaches and late dinners.

    Typical December: highs of 15°C, some rain
    • Beach
    • Old town

    Swap this stop

  8. BCN→ORD Thu 10 Dec leaves 18:05Lands at O'Hare International Airport. 1 stop, TAP Air Portugal first, check the travel time and bag rules€318seen 2 days ago Check price
    • it has stops, so check when it lands before you book anything after it

  9. Chicago

    United States, Home, Thu 10 Dec

We count up to €65 a bag on each of the 2 long flights; check the airlines' prices.

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.

Open this tripSeparate tickets: if one flight is late or cancelled, the next airline won't wait.
Trip page

ChicagoBarcelona5nBologna4nLisbon4nChicago

4 flights, 3 countries in Europe, 13 nights, 27 Nov – 11 Dec.

All three places have old towns. Typical November and December highs run from 8°C in Bologna to 18°C in Barcelona.

about€828per person, with a cabin bag

€650 without bags, plus €178 in cabin bags · prices seen up to 3 days ago, may be higher now

See the flightsHide the flights

  1. Chicago

    United States, Start, Fri 27 Nov

  2. ORD→BCN Fri 27 Nov leaves 20:10Leaves from O'Hare International Airport. 1 stop, TAP Air Portugal first, check the travel time and bag rules€273seen 2 days ago Check price
    • it may land Sat 28 Nov: check the time before you book your first night in Barcelona

  3. Barcelona

    Spain, 5 nights, 28 Nov – 3 Dec

    Catalonia's capital on the Mediterranean, known for Gaudí's Sagrada Família and Park Güell, the Gothic Quarter, city beaches and late dinners.

    Typical November: highs of 18°C, some rain
    • Beach
    • Old town

    Swap this stop

  4. BCN→BLQ Thu 3 Dec leaves 06:30, lands 08:15Ryanair, about 2 hours, cabin bag about €24€21 Check price
    • a price seen 3 days ago: it may be higher now or sold out

  5. Bologna

    Italy, 4 nights, 3–7 Dec

    The capital of Emilia-Romagna, with miles of porticoed streets, two leaning medieval towers, Europe's oldest university and some of Italy's best food.

    Typical December: highs of 8°C, some rain
    • Old town

    Swap this stop

  6. BLQ→LIS Mon 7 Dec leaves 05:45, lands 07:50 early startMalta Air, about 3 hours, cabin bag about €24€35seen 2 days ago Check price

  7. Lisbon

    Portugal, 4 nights, 7–11 Dec

    Portugal's capital, on hills above the Tagus, with old trams, tiled facades, fado bars in Alfama, the monastery at Belém and Atlantic beaches a short ride away.

    Typical December: highs of 15°C, wet
    • Capital
    • Old town

    Swap this stop

  8. LIS→ORD Fri 11 Dec leaves 11:55Lands at O'Hare International Airport. Non-stop, TAP Air Portugal, about 9½ hours, cabin bag often extra on long-haul fares: we count about €65€321 Check price
    • a price seen 3 days ago: it may be higher now or sold out

  9. Chicago

    United States, Home, Fri 11 Dec

We count up to €65 a bag on each of the 2 long flights; check the airlines' prices.

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.

Open this tripSeparate tickets: if one flight is late or cancelled, the next airline won't wait.
Trip page

ChicagoMilan4nAlicante4nLisbon5nChicago

4 flights, 3 countries in Europe, 13 nights, 27 Nov – 11 Dec.

Lisbon is a capital and Alicante is on the coast. Typical November and December highs run from 12°C in Milan to 18°C in Alicante.

about€840per person, with a cabin bag

€662 without bags, plus €178 in cabin bags · prices seen up to 6 days ago, may be higher now

See the flightsHide the flights

  1. Chicago

    United States, Start, Fri 27 Nov

  2. ORD→MXP Fri 27 Nov leaves 20:10Leaves from O'Hare International Airport, lands at Milano Malpensa Airport. 1 stop, TAP Air Portugal first, check the travel time and bag rules€277 Check price
    • a price seen 3 days ago: it may be higher now or sold out
    • it may land Sat 28 Nov: check the time before you book your first night in Milan

  3. Milan

    Italy, 4 nights, 28 Nov – 2 Dec

    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

  4. MXP→ALC Wed 2 Dec leaves 19:15, lands 21:25Leaves from Milano Malpensa Airport. Ryanair, about 2 hours, cabin bag about €24€18 Check price
    • a price seen 4 days ago: it may be higher now or sold out

  5. Alicante

    Spain, 4 nights, 2–6 Dec

    A Costa Blanca port city below a hilltop castle, with a palm-lined seafront, a sandy town beach and tapas bars in the old quarter. More beaches line the coast in both directions.

    Typical December: highs of 18°C, dry
    • Beach

    Swap this stop

  6. ALC→LIS Sun 6 Dec leaves 19:40, lands 20:30Ryanair, about 2 hours, cabin bag about €24€46 Check price
    • a price seen 6 days ago: it may be higher now or sold out

  7. Lisbon

    Portugal, 5 nights, 6–11 Dec

    Portugal's capital, on hills above the Tagus, with old trams, tiled facades, fado bars in Alfama, the monastery at Belém and Atlantic beaches a short ride away.

    Typical December: highs of 15°C, wet
    • Capital
    • Old town

    Swap this stop

  8. LIS→ORD Fri 11 Dec leaves 11:55Lands at O'Hare International Airport. Non-stop, TAP Air Portugal, about 9½ hours, cabin bag often extra on long-haul fares: we count about €65€321 Check price
    • a price seen 3 days ago: it may be higher now or sold out

  9. Chicago

    United States, Home, Fri 11 Dec

We count up to €65 a bag on each of the 2 long flights; check the airlines' prices.

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.

Open this tripSeparate tickets: if one flight is late or cancelled, the next airline won't wait.
Trip page

ChicagoWarsaw3nDublin5nStockholm4nChicago

4 flights, 3 countries in Europe, 12 nights, 1–15 Dec.

All three places are capitals. Typical December highs run from 2°C in Warsaw to 9°C in Dublin.

about€862per person, with a cabin bag

€684 without bags, plus €178 in cabin bags · prices seen up to 8 days ago, may be higher now

See the flightsHide the flights

  1. Chicago

    United States, Start, Tue 1 Dec

  2. ORD→WMI Tue 1 Dec leaves 18:30Leaves from O'Hare International Airport. 2 stops, Icelandair first, check the travel time and bag rules€279seen 2 days ago Check price
    • Warsaw-Modlin Airport is 35 km from Warsaw · Far airports compared
    • it may land Wed 2 Dec: check the time before you book your first night in Warsaw

  3. Warsaw

    Poland, 3 nights, 2–5 Dec

    Poland's capital on the Vistula, with an old town rebuilt brick by brick after the war, strong history museums, riverside bars and a growing food scene.

    Typical December: highs of 2°C, some rain
    • Capital
    • Old town

    Swap this stop

  4. WMI→DUB Sat 5 Dec leaves 06:45, lands 08:50Ryanair, about 3 hours, cabin bag about €24€31 Check price
    • Warsaw-Modlin Airport is 35 km from Warsaw · Far airports compared
    • a price seen 8 days ago: it may be higher now or sold out

  5. Dublin

    Ireland, 5 nights, 5–10 Dec

    Ireland's capital on the River Liffey, known for its pubs and live music, Georgian squares, Trinity College's old library and sea swimming spots along the bay.

    Typical December: highs of 9°C, some rain
    • Capital

    Swap this stop

  6. DUB→ARN Thu 10 Dec leaves 20:45, lands 00:20 the next day late landingLands at Stockholm Arlanda Airport. Malta Air, about 2½ hours, cabin bag about €24€15 Check price
    • a price seen 4 days ago: it may be higher now or sold out

  7. Stockholm

    Sweden, 4 nights, 11–15 Dec

    Sweden's capital, built across islands where Lake Mälaren meets the Baltic, with the old town of Gamla Stan, the Vasa ship museum and archipelago boat trips.

    Typical December: highs of 3°C, some rain
    • Capital
    • Lakes
    • Old town

    Swap this stop

  8. ARN→ORD Tue 15 Dec leaves 14:20Leaves from Stockholm Arlanda Airport, lands at O'Hare International Airport. 1 stop, TAP Air Portugal first, check the travel time and bag rules€359 Check price
    • a price seen 3 days ago: it may be higher now or sold out
    • it has stops, so check when it lands before you book anything after it

  9. Chicago

    United States, Home, Tue 15 Dec

We count up to €65 a bag on each of the 2 long flights; check the airlines' prices.

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.

Open this tripSeparate tickets: if one flight is late or cancelled, the next airline won't wait.
Trip page

ChicagoParis4nMilan5nMadrid4nChicago

4 flights, 3 countries in Europe, 13 nights, 2–16 Dec.

Two of the three places are capitals and Madrid has an old town. Typical December highs are 7–10°C at every stop.

about€868per person, with a cabin bag

€690 without bags, plus €178 in cabin bags · prices seen up to 4 days ago, may be higher now

See the flightsHide the flights

  1. Chicago

    United States, Start, Wed 2 Dec

  2. ORD→ORY Wed 2 Dec leaves 19:00Leaves from O'Hare International Airport, lands at Paris Orly Airport. 1 stop, TAP Air Portugal first, check the travel time and bag rules€271seen 2 days ago Check price
    • you leave Paris from a different airport (BVA, Beauvais-Tille Airport)
    • it may land Thu 3 Dec: check the time before you book your first night in Paris

  3. Paris

    France, 4 nights, 3–7 Dec

    France's capital on the Seine, with the Louvre, the Eiffel Tower, Notre-Dame, café terraces, neighbourhood markets and some of the world's best museums.

    Typical December: highs of 8°C, some rain
    • Capital

    Swap this stop

  4. BVA→BGY Mon 7 Dec leaves 06:00, lands 07:30Malta Air, about 1½ hours, cabin bag about €24€25seen 2 days ago Check price
    • Beauvais-Tille Airport is 69 km from Paris · Far airports compared
    • Orio al Serio International Airport is 46 km from Milan · Far airports compared
    • you leave Milan from a different airport (MXP, Milano Malpensa Airport)

  5. Milan

    Italy, 5 nights, 7–12 Dec

    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 December: highs of 7°C, some rain

    Swap this stop

  6. MXP→MAD Sat 12 Dec leaves 17:25, lands 19:45Leaves from Milano Malpensa Airport. Malta Air, about 2½ hours, cabin bag about €24€26 Check price
    • a price seen 4 days ago: it may be higher now or sold out

  7. Madrid

    Spain, 4 nights, 12–16 Dec

    Spain's capital on the high central plateau, with the Prado and Reina Sofía museums, the Retiro park, late-night tapas and the Guadarrama mountains an hour north.

    Typical December: highs of 10°C, some rain
    • Capital
    • Old town
    • Ski

    Swap this stop

  8. MAD→ORD Wed 16 Dec leaves 06:30Lands at O'Hare International Airport. 1 stop, Air Europa first, check the travel time and bag rules€368 Check price
    • a price seen 4 days ago: it may be higher now or sold out

  9. Chicago

    United States, Home, Wed 16 Dec

We count up to €65 a bag on each of the 2 long flights; check the airlines' prices.

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.

Open this tripSeparate tickets: if one flight is late or cancelled, the next airline won't wait.
Trip page

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