United States

A weekend in Chicago

Friday evening to Sunday afternoon in Chicago, planned around the fact that you arrive tired and leave in a hurry.

  • 2 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

3 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

    Steppenwolf Theatre Company

    Picked because you chose culture & museums + balanced energy

    • 2h 30m
    • Culture & museums

    theater and theater company in Chicago, Illinois, United States

    North Halsted Street 1650, 60614 Chicago

    Show on map

    Sources: OpenStreetMap · Wikidata · Wikivoyage

Day 2

11 of 24 hours planned

  1. 08:0008:45

    Cafe Jumping Bean

    Suggested because you chose food

    • 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

    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

    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

Departure day

4 of 24 hours planned

  1. 08:0008:45

    Kopi Cafe

    Suggested because you chose food

    • 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

    Indian Boundary Park

    Picked because you chose local experiences + balanced energy

    • 1h 30m
    • Local experiences

    park in Chicago, Illinois

    West Lunt Avenue 2500, 60645 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 it fits a mid-range budget

    • 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. 14:30

    You leave

Sources

  • Wikidata
  • © OpenStreetMap contributors