Luyaro

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

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  3. 14:3017:00

    Nederlander Theatre

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    theater in Chicago, Illinois

    West Randolph Street 24, 60601 Chicago

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

  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

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  6. 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

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

Day 2

11 of 24 hours planned

  1. 08:0008:45

    Cafe Jumping Bean

    Picked because you chose food + balanced energy

    • 45m
    • Meal

    West 18th Street 1439, 60608 Chicago

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

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  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

    Show on map

    Sources: OpenStreetMap · Wikidata

  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

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  6. 14:3017:00

    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

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

  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

    Show on map

    Sources: OpenStreetMap

  9. 20:3022:00

    Elephant & Castle

    Picked because you chose local experiences + balanced energy

    • 1h 30m
    • Local experiences

    West Adams Street 111, 60603 Chicago

    Show on map

    Sources: OpenStreetMap · Wikivoyage

Day 3

10 of 24 hours planned

  1. 08:0008:45

    Kopi Cafe

    Picked because you chose food + balanced energy

    • 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

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  2. 08:45

    45m open

    08:45 – 09:30

    Nothing planned here. That was on purpose.

  3. 09:3011:00

    Aragon Ballroom

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

    • 1h 30m
    • Culture & museums

    ballroom in Chicago, Illinois

    West Lawrence Avenue 1106, 60640 Chicago

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

  4. 11:00

    2h open

    11:00 – 13:00

    Nothing planned here. That was on purpose.

  5. 13:0014:00

    Nigerian Kitchen

    Suggested because you chose food

    • 1h
    • Meal

    North Broadway 4447, 60640 Chicago

    Opening hours: Mon–Sat 11:00–22:00 · Sun 12:00–20:00

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  6. 14:3017:00

    Emil Bach House

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    house in Chicago, Illinois

    7415 N Sheridan Rd

    Show on map

    Sources: Wikidata · Wikivoyage

  7. 17:00

    2h open

    17:00 – 19:00

    Nothing planned here. That was on purpose.

  8. 19:0020:30

    Silver Seafood

    Suggested because you chose food

    • 1h 30m
    • Meal

    North Broadway 4829, 60640 Chicago

    Opening hours: Mon–Tue 11:00–22:00 · Wed closed · Thu–Sun 11:00–22:00

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  9. 20:3022:00

    Hopleaf Bar

    Picked because you chose food and local experiences + balanced energy

    • 1h 30m
    • Food

    North Clark Street 5148, 60640 Chicago

    Opening hours: Mon–Thu 12:00–23:00 · Fri–Sat 12:00–00:00 · Sun 12:00–22:00

    Show on map

    Sources: OpenStreetMap · Wikivoyage

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

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  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

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

  4. 12:00

    1h open

    12:00 – 13:00

    Nothing planned here. That was on purpose.

  5. 13:0014:00

    Frontera Grill

    Suggested because it fits a mid-range budget

    • 1h
    • Meal

    restaurant in Chicago, Illinois, USA

    North Clark Street 445, 60654 Chicago

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

  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

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

  7. 17:0019:30

    Hull House

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    settlement house in Chicago, Illinois, United States

    South Halsted Street 800, 60607 Chicago

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

  8. 19:3021:00

    The Publican

    Suggested because you chose food

    • 1h 30m
    • Meal

    West Fulton Market 837, 60607 Chicago

    Show on map

    Sources: OpenStreetMap

  9. 21:0023:30

    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

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

Day 5

Departure day

5 of 24 hours planned

  1. 08:0008:45

    Black Dog Gelato

    Picked because you chose food + balanced energy

    • 45m
    • Meal

    North Damen Avenue 859, 60622-4907 Chicago

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

    Show on map

    Sources: OpenStreetMap · Wikivoyage

  2. 08:45

    45m open

    08:45 – 09:30

    Nothing planned here. That was on purpose.

  3. 09:3012:00

    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

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

  4. 12:00

    1h open

    12:00 – 13:00

    Nothing planned here. That was on purpose.

  5. 13:0014:00

    Smyth

    Suggested because you chose food

    • 1h
    • 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

    Show on map

    Sources: OpenStreetMap

  6. 14:30

    You leave

Sources

  • Wikidata
  • © OpenStreetMap contributors