WiseJourney

United States

Five days in Chicago

Long enough to leave the centre. Five days in Chicago with one day that is not about Chicago at all.

  • 4 nights
  • Couple
  • Balanced pace
  • Mid-range budget
Plan your own Chicago trip

Every place here was checked on 2026-10-27 or later, and each one says where it came from.

The plan, day by day

5 days

Day 1

Arrival day

8 of 24 hours planned

  1. 09:30

    You arrive

  2. 13:0014:00

    Miller’s Pub

    Suggested because you chose food

    • 1h
    • Meal

    South Wabash Avenue 134, 60603 Chicago

    Opening hours: Mon–Sun 11:00–02:00

  3. 14:3017:00

    National Hellenic Museum

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    Museum about Greek-American heritage in Chicago, Illinois

    South Halsted Street 333, 60661 Chicago

  4. 17:00

    2h open

    17:00 – 19:00

    Nothing planned here. That was on purpose.

  5. 19:0020:30

    Emerald Loop

    Suggested because you chose food

    • 1h 30m
    • Meal

    North Wabash Avenue 216, 60601 Chicago

  6. 20:3023:00

    Civic Opera House

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    opera house in Chicago, Illinois, United States

    North Wacker Dr 20, 60606 Chicago

Day 2

12 of 24 hours planned

  1. 08:0008:45

    Cafe Jumping Bean

    Suggested because it fits a mid-range budget

    • 45m
    • Meal

    West 18th Street 1439, 60608 Chicago

    Opening hours: Mon–Sat 06:00–19:00 · Sun 06:30–19:00

  2. 08:45

    45m open

    08:45 – 09:30

    Nothing planned here. That was on purpose.

  3. 09:3012:00

    Museum of Broadcast Communications

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    museum

    West Randolph Street 440, 60606 Chicago

  4. 12:00

    1h open

    12:00 – 13:00

    Nothing planned here. That was on purpose.

  5. 13:0014:00

    Eleven City Diner

    Suggested because you chose food

    • 1h
    • Meal

    South Wabash Avenue 1112, 60605 Chicago

  6. 14:3017:00

    Biograph Theater

    Picked because you chose culture & museums and local experiences + balanced energy

    • 2h 30m
    • Culture & museums

    theater and former movie theater in Chicago, Illinois, United States

    North Lincoln Avenue 2433, 60614 Chicago

  7. 17:00

    2h open

    17:00 – 19:00

    Nothing planned here. That was on purpose.

  8. 19:0020:30

    Girl & The Goat

    Suggested because you chose food

    • 1h 30m
    • Meal

    West Randolph Street 809, 60607 Chicago

    Opening hours: Mon–Thu 16:30–23:00 · Fri–Sat 16:30–00:00 · Sun 16:30–23:00

  9. 20:3023:00

    Auditorium Theatre

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    theater and music venue inside the Auditorium Building in Chicago, Illinois, United States

    East Ida B. Wells Drive 50, 60605 Chicago

Day 3

12 of 24 hours planned

  1. 08:0008:45

    Kopi Cafe

    Suggested because it fits a mid-range budget

    • 45m
    • Meal

    North Clark Street 5317, 60640 Chicago

    Opening hours: Mon–Thu 10:00–19:00 · Fri–Sat 10:00–20:00 · Sun 10:00–19:00

  2. 08:45

    45m open

    08:45 – 09:30

    Nothing planned here. That was on purpose.

  3. 09:3012:00

    Art Institute of Chicago

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    art museum and school in Chicago, United States

    South Michigan Avenue 111, 60603 Chicago

    Opening hours: Mon 11:00–17:00 · Tue–Wed closed · Thu 11:00–20:00 · Fri–Sun 11:00–17:00

  4. 12:00

    1h open

    12:00 – 13:00

    Nothing planned here. That was on purpose.

  5. 13:0014:00

    Frontera Grill

    Suggested because you chose food

    • 1h
    • Meal

    restaurant in Chicago, Illinois, USA

    North Clark Street 445, 60654 Chicago

  6. 14:3017:00

    Garfield Park Conservatory

    Picked because you chose local experiences + balanced energy

    • 2h 30m
    • Local experiences

    greenhouse conservatory in Chicago, US

    North Central Park Avenue 300, 60624 Chicago

  7. 17:00

    2h open

    17:00 – 19:00

    Nothing planned here. That was on purpose.

  8. 19:0020:30

    The Publican

    Suggested because you chose food

    • 1h 30m
    • Meal

    West Fulton Market 837, 60607 Chicago

  9. 20:3023:00

    Studebaker Theater

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    building in Chicago, Illinois, United States

    South Michigan Avenue 410, 60605 Chicago

Day 4

15 of 24 hours planned

  1. 08:0008:45

    Fei Da Bakery

    Suggested because you chose food

    • 45m
    • Meal

    South Wentworth Avenue 2228, 60616 Chicago

  2. 08:45

    45m open

    08:45 – 09:30

    Nothing planned here. That was on purpose.

  3. 09:3012:00

    Chicago Architecture Center

    Picked because you chose culture & museums and local experiences + balanced energy

    • 2h 30m
    • Culture & museums

    nonprofit cultural organization based in Chicago, Illinois, United States

    East Wacker Drive 111, 60601 Chicago

    Opening hours: Mon–Tue 10:00–17:00 · Wed–Sat 10:00–19:00 · Sun 10:00–17:00

  4. 12:00

    1h open

    12:00 – 13:00

    Nothing planned here. That was on purpose.

  5. 13:0014:00

    Oriole

    Suggested because it fits a mid-range budget

    • 1h
    • Meal

    restaurant in Chicago

    West Walnut Street 661, 60661 Chicago

    Opening hours: Mon closed · Tue–Sat 17:30–21:30 · Sun closed

  6. 14:3017:00

    Museum of Contemporary Photography

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    museum in Chicago, Illinois

    600 S Michigan Ave

  7. 17:0019:30

    Kenneth C. Griffin Museum of Science and Industry

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    museum in Chicago, Illinois, United States

    South Lake Shore Drive 5700, 60637 Chicago

  8. 19:3021:00

    Smyth

    Suggested because you chose food

    • 1h 30m
    • Meal

    Smyth is a restaurant located in Chicago, currently the only one holding three Michelin stars. Smyth is located on the second floor above a bar called The Loyalist also operated by Smyth's owners.

    North Ada Street 177, 60607 Chicago

    Opening hours: Mon closed · Tue–Sat 17:00–22:00 · Sun closed

  9. 21:0023:30

    Nederlander Theatre

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    theater in Chicago, Illinois

    West Randolph Street 24, 60601 Chicago

Day 5

Departure day

5 of 24 hours planned

  1. 08:0008:45

    Black Dog Gelato

    Suggested because it fits a mid-range budget

    • 45m
    • Meal

    North Damen Avenue 859, 60622-4907 Chicago

    Opening hours: Mon–Sun 14:00–22:00

  2. 08:45

    45m open

    08:45 – 09:30

    Nothing planned here. That was on purpose.

  3. 09:3012:00

    Barack Obama Presidential Center

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    presidential museum in Chicago, Illinois

    South Stony Island Avenue 6001, 60637 Chicago

  4. 12:00

    1h open

    12:00 – 13:00

    Nothing planned here. That was on purpose.

  5. 13:0014:00

    Kasama

    Suggested because you chose food

    • 1h
    • Meal

    Kasama is a Filipino restaurant in Chicago, Illinois. The restaurant has received two Michelin stars, making it the world's first Filipino restaurant to earn one.

    North Winchester Avenue 1001, 60622 Chicago

  6. 14:30

    You leave

Sources

  • Wikidata
  • © OpenStreetMap contributors