FareDice / Start cities / Chicago

Cheap multi-country trips in Europe from Chicago

Right now €301 in flights buys a trip from Chicago to London and on through 3 countries in Europe, leaving in the next month. 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.

Not in Chicago? From South Bend (111 km), Milwaukee (121 km), Lafayette (173 km), Kalamazoo (176 km), Muskegon (183 km), Bloomington (189 km) or any airport within 1,000 km, these trips start here: getting to Chicago is on you.

The cheapest trip of each length

ChicagoLondon2nGothenburg3nGdansk

3 flights, 3 countries, 5 nights, 20–26 Oct. See the flightsHide the flights

€301about €349 with a cabin bag (+ 1 leg to check)

  1. Chicago

    United States, Start, Tue 20 Oct

  2. MDW→LGW Tue 20 OctFrom Chicago Midway International Airport, into London Gatwick Airport. 1 stop, starting with Southwest Airlines, cabin bag: check€264seen 4 days ago Check price
    • you leave London from a different airport (STN, Stansted Airport)
    • overnight: it lands on Wed 21 Oct, so your nights in London count from then

  3. London

    United Kingdom, 2 nights, 21–23 Oct

    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 October: highs of 16°C, some rain
    • Capital
    • Old town

    Swap this stop

  4. STN→GOT Fri 23 OctRyanair, cabin bag about €24€22seen yesterday Check price
    • Stansted Airport is 50 km from London

  5. Gothenburg

    Sweden, 3 nights, 23–26 Oct

    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 October: highs of 12°C, wet

    Swap this stop

  6. GOT→GDN Mon 26 OctRyanair, cabin bag about €24€15seen 3 days ago Check price

  7. Gdansk

    Poland, Last stop, Mon 26 Oct

    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 October: highs of 13°C, some rain

    Swap this stop

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

ChicagoLondon2nGothenburg3nGdansk2nBratislava

4 flights, 4 countries, 7 nights, 20–28 Oct. See the flightsHide the flights

€317about €389 with a cabin bag (+ 1 leg to check)

  1. Chicago

    United States, Start, Tue 20 Oct

  2. MDW→LGW Tue 20 OctFrom Chicago Midway International Airport, into London Gatwick Airport. 1 stop, starting with Southwest Airlines, cabin bag: check€264seen 4 days ago Check price
    • you leave London from a different airport (STN, Stansted Airport)
    • overnight: it lands on Wed 21 Oct, so your nights in London count from then

  3. London

    United Kingdom, 2 nights, 21–23 Oct

    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 October: highs of 16°C, some rain
    • Capital
    • Old town

    Swap this stop

  4. STN→GOT Fri 23 OctRyanair, cabin bag about €24€22seen yesterday Check price
    • Stansted Airport is 50 km from London

  5. Gothenburg

    Sweden, 3 nights, 23–26 Oct

    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 October: highs of 12°C, wet

    Swap this stop

  6. GOT→GDN Mon 26 OctRyanair, cabin bag about €24€15seen 3 days ago Check price

  7. Gdansk

    Poland, 2 nights, 26–28 Oct

    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 October: highs of 13°C, some rain

    Swap this stop

  8. GDN→BTS Wed 28 OctRyanair, cabin bag about €24€16seen 2 days ago Check price

  9. Bratislava

    Slovakia, Last stop, Wed 28 Oct

    Slovakia's capital on the Danube, with a white hilltop castle, a compact old town of cafés and the Little Carpathians vineyards and hills nearby.

    Typical October: highs of 16°C, some rain
    • Capital

    Swap this stop

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

ChicagoLondon2nGothenburg3nGdansk2nBratislava3nRome

5 flights, 5 countries, 10 nights, 20–31 Oct. See the flightsHide the flights

€329about €435 with a cabin bag (+ 1 leg to check)

  1. Chicago

    United States, Start, Tue 20 Oct

  2. MDW→LGW Tue 20 OctFrom Chicago Midway International Airport, into London Gatwick Airport. 1 stop, starting with Southwest Airlines, cabin bag: check€264seen 4 days ago Check price
    • you leave London from a different airport (STN, Stansted Airport)
    • overnight: it lands on Wed 21 Oct, so your nights in London count from then

  3. London

    United Kingdom, 2 nights, 21–23 Oct

    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 October: highs of 16°C, some rain
    • Capital
    • Old town

    Swap this stop

  4. STN→GOT Fri 23 OctRyanair, cabin bag about €24€22seen yesterday Check price
    • Stansted Airport is 50 km from London

  5. Gothenburg

    Sweden, 3 nights, 23–26 Oct

    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 October: highs of 12°C, wet

    Swap this stop

  6. GOT→GDN Mon 26 OctRyanair, cabin bag about €24€15seen 3 days ago Check price

  7. Gdansk

    Poland, 2 nights, 26–28 Oct

    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 October: highs of 13°C, some rain

    Swap this stop

  8. GDN→BTS Wed 28 OctRyanair, cabin bag about €24€16seen 2 days ago Check price

  9. Bratislava

    Slovakia, 3 nights, 28–31 Oct

    Slovakia's capital on the Danube, with a white hilltop castle, a compact old town of cafés and the Little Carpathians vineyards and hills nearby.

    Typical October: highs of 16°C, some rain
    • Capital

    Swap this stop

  10. BTS→FCO Sat 31 OctInto Leonardo da Vinci-Fiumicino Airport. Wizz Air, cabin bag about €34€12seen 5 days ago Check price

  11. Rome

    Italy, Last stop, Sat 31 Oct

    Italy's capital, with the Colosseum, the Forum, the Pantheon, the Vatican museums, baroque piazzas and trattorias serving carbonara and cacio e pepe.

    Typical October: highs of 23°C, some rain
    • Capital
    • Old town

    Swap this stop

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

There and back

The cheapest trip we found that ends with the flight home to Chicago: €667 in flights.

ChicagoParis4nMilan2nMadrid4nChicago

4 flights, 3 countries, 10 nights, 24 Oct – 4 Nov. See the flightsHide the flights

€667about €725 with a cabin bag (+ 2 legs to check)

  1. Chicago

    United States, Start, Sat 24 Oct

  2. ORD→CDG Sat 24 OctFrom O'Hare International Airport, into Charles de Gaulle Airport. 1 stop, starting with JetBlue, cabin bag: check€325seen 3 days ago Check price
    • you leave Paris from a different airport (BVA, Beauvais-Tille Airport)
    • overnight: it lands on Sun 25 Oct, so your nights in Paris count from then

  3. Paris

    France, 4 nights, 25–29 Oct

    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 October: highs of 17°C, some rain
    • Capital
    • Old town

    Swap this stop

  4. BVA→BGY Thu 29 OctRyanair, cabin bag about €24€18seen yesterday Check price
    • Beauvais-Tille Airport is 69 km from Paris
    • Orio al Serio International Airport is 46 km from Milan
    • you leave Milan from a different airport (MXP, Milano Malpensa Airport)

  5. Milan

    Italy, 2 nights, 29–31 Oct

    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 October: highs of 19°C, some rain
    • Old town

    Swap this stop

  6. MXP→MAD Sat 31 OctFrom Milano Malpensa Airport. Wizz Air Malta, cabin bag about €34€16seen 5 days ago Check price

  7. Madrid

    Spain, 4 nights, 31 Oct – 4 Nov

    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 October: highs of 20°C, some rain
    • Capital
    • Old town

    Swap this stop

  8. MAD→ORD Wed 4 NovInto O'Hare International Airport. 1 stop, starting with TAP Air Portugal, cabin bag: check€308seen 3 days ago Check price

  9. Chicago

    United States, Home, Wed 4 Nov

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

Where Chicago's fares land

The cheapest fare we've seen lately from Chicago to each city, over the next month. Trips go on from these.

On these trips

Trips from Bratislava, Gdansk, Gothenburg, London, Madrid, Milan, Paris, Rome. Trips through France, Italy, Poland, Slovakia, Spain, Sweden, United Kingdom.

The basicsstart here
Leave betweenand
PlacestoAny: from 1 up to 12.
Trip shapeoptional
Nights in each placetoAny: from 1 up to 14.
Trip length, first flight to lastto
Finish Anywhere: the flight home isn't counted. A finish city isn't counted as a place.
Which placesoptional
Places you must visit (up to 3)
Kind of places From our notes on each city. Ski counts from December to mid-April. Start, return and must-visit cities don't count. Mixing them up compares the kinds you pick, or capitals, islands and beaches.
Only these countries
A deep dive: at leastcities in
Skip countries
Flights and youoptional
Passports you holdLeaves out countries that need a visa.

Prices are flights only, the cheapest seen lately. Each trip shows its total with a cabin bag.