Budget-Friendly Weekly Guide

    Things to Do in Chicago This Week

    Sep 14–20, 2026 Chicago, Illinois8 events · 29 activities
    9 under $20

    Looking for fun things to do in Chicago this week? We've curated 37+ budget-friendly picks — concerts, tours, family activities, and free entry events from Sep 14–20, 2026, sorted by date.

    Live Events This Week

    Riot Fest 2026 - Sunday

    Riot Fest 2026 - Sunday

    Sun, Sep 20
    Douglass Park
    Chicago Bears vs. Minnesota Vikings

    Chicago Bears vs. Minnesota Vikings

    Sun, Sep 20
    Soldier Field
    Chicago White Sox vs. Detroit Tigers

    Chicago White Sox vs. Detroit Tigers

    Sun, Sep 20
    Rate Field
    Nick Warren - Ages 21+

    Nick Warren - Ages 21+

    Sun, Sep 20
    Castaways
    Mike Wheeler Blues Band/Omar Coleman Blues Band

    Mike Wheeler Blues Band/Omar Coleman Blues Band

    Under $20
    Sun, Sep 20
    Kingston Mines - Chicago Blues Center
    Domingo De Lucha Libre

    Domingo De Lucha Libre

    Sun, Sep 20
    Avondale Music Hall
    Jimmy Dore Show

    Jimmy Dore Show

    Sun, Sep 20
    Zanies Comedy Club - Chicago
    Cheerleader Roadkill - Ages 17+

    Cheerleader Roadkill - Ages 17+

    Sun, Sep 20
    Subterranean

    Activities & Experiences We Sell in Chicago

    Chicago Premier Bottomless Mimosa Brunch Cruise on Lake Michigan

    Chicago Premier Bottomless Mimosa Brunch Cruise on Lake Michigan

    $94
    Chicago
    Highlights of Chicago Private Tour with 360 Observation Deck Tickets

    Highlights of Chicago Private Tour with 360 Observation Deck Tickets

    $369
    Chicago
    Signature Lunch Cruise on Lake Michigan

    Signature Lunch Cruise on Lake Michigan

    $78
    Chicago
    Fireworks Signature Dinner Cruise on Lake Michigan

    Fireworks Signature Dinner Cruise on Lake Michigan

    $205
    Chicago
    Premier Plus Architectural Lunch Cruise on the Chicago River

    Premier Plus Architectural Lunch Cruise on the Chicago River

    $104
    Chicago
    Fireworks Premier Dinner Cruise on Lake Michigan

    Fireworks Premier Dinner Cruise on Lake Michigan

    $243
    Chicago
    The Field Museum - Basic Admission

    The Field Museum - Basic Admission

    $26
    Chicago
    Chicago Premier Plus Bottomless Mimosa Architectural Brunch Cruise on the Chicag

    Chicago Premier Plus Bottomless Mimosa Architectural Brunch Cruise on the Chicag

    $142
    Chicago
    AAA/CAA Member: Big Bus Chicago Hop-On Hop-Off Tour

    AAA/CAA Member: Big Bus Chicago Hop-On Hop-Off Tour

    Chicago
    Downtown Chicago TV and Movie Sites - Walking Tour

    Downtown Chicago TV and Movie Sites - Walking Tour

    $37
    Chicago
    Chicago CityPASS® - Access to 5 Attractions

    Chicago CityPASS® - Access to 5 Attractions

    $128
    Chicago
    Chicago Food Tour

    Chicago Food Tour

    $117
    Chicago
    Chicago Signature Bottomless Mimosa Brunch Cruise on Lake Michigan

    Chicago Signature Bottomless Mimosa Brunch Cruise on Lake Michigan

    Chicago
    Chicago Premier Plus Dinner Cruise on the Chicago River

    Chicago Premier Plus Dinner Cruise on the Chicago River

    $122
    Chicago
    Go City - Chicago Explorer Pass - Access to up to 7 Attractions

    Go City - Chicago Explorer Pass - Access to up to 7 Attractions

    $84
    Chicago
    Special Discount Offer: Big Bus Chicago Hop-On Hop-Off Tour

    Special Discount Offer: Big Bus Chicago Hop-On Hop-Off Tour

    $58
    Chicago
    Hard Rock Cafe Chicago

    Hard Rock Cafe Chicago

    $36
    Chicago
    Sights & Sips Cruise on the Chicago River

    Sights & Sips Cruise on the Chicago River

    $92
    Chicago
    Chicago Tour: The Hopper Heist - City Exploration Game

    Chicago Tour: The Hopper Heist - City Exploration Game

    Under $20
    Chicago
    Signature Dinner Cruise on Lake Michigan

    Signature Dinner Cruise on Lake Michigan

    $100
    Chicago
    SmartSIM USA - eSIM All Access Pass

    SmartSIM USA - eSIM All Access Pass

    Under $20
    Chicago
    Chicago Premier Lunch Cruise on Lake Michigan

    Chicago Premier Lunch Cruise on Lake Michigan

    $94
    Chicago
    Total Chicago: From Architecture to Food - Half-Day Tour

    Total Chicago: From Architecture to Food - Half-Day Tour

    $90
    Chicago
    Chicago Night Crime - Guided Bus Tour

    Chicago Night Crime - Guided Bus Tour

    $47
    Chicago
    Chicago Culture and Architecture

    Chicago Culture and Architecture

    $81
    Chicago
    Chicago Crime - Guided Bus Tour

    Chicago Crime - Guided Bus Tour

    $42
    Chicago
    Go City - Chicago All-Inclusive Pass - Up to 5 Days of Access to 30+ Attractions

    Go City - Chicago All-Inclusive Pass - Up to 5 Days of Access to 30+ Attractions

    $149
    Chicago
    Chicago Premier Dinner Cruise on Lake Michigan

    Chicago Premier Dinner Cruise on Lake Michigan

    $128
    Chicago
    The Field Museum

    The Field Museum

    $38
    Chicago

    More cheap fun in Chicago

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