Deals

Happy hour deals

Restaurants and bars in Chicago. Open a card for the window, what it covers, and the page we copied it from.

ADVERTINYPin your listing at the topFirst card in the directory. Shoppers scanning every house in town.See rates

RPM Italian River North

Drink+foodWeekdays 4–6 at the barlive

Weekdays 4–6 at the bar. $8 cicchetti, $8 signature cocktails and wines by the glass, $5 beer, $15 burrata raviolo.

Cite: rpmrestaurants.com · Updated 2026-09-02

River Northlive

RPM Steak River North

Drink+foodWeekdays 4–5:30 at the Proper Barlive

Weekdays 4–5:30 at the Proper Bar. $10 cocktails and wines, $5 beers and minis, bar snacks from $12.

Cite: rpmrestaurants.com · Updated 2026-09-02

River Northlive

Gilt Bar River North

Drink+foodDaily until 5pmlive

Daily until 5pm. $6.99 sliders and fries, $6 wine and draft beer, $7 highballs and teeny martinis, $8 Old Fashioned.

Cite: giltbarchicago.com · Updated 2026-09-02

River Northlive

Shaw's Crab House River North

Drink+foodMon–Fri 3–5 in the Oyster Barlive

Mon–Fri 3–5 in the Oyster Bar. Oysters $12 half dozen / $24 dozen, $5 draft beer, $15 mini lobster rolls.

Cite: shawscrabhouse.com · Updated 2026-09-02

River Northlive

Bar Siena West Loop

Drink+foodMon–Fri 3:30–5:30live

Mon–Fri 3:30–5:30. $9 cocktails, $10 wine, $4 sliders, $12 pizza.

Cite: barsienawestloop.com · Updated 2026-09-02

West Looplive

Monteverde West Loop

Drink+foodTue–Sat 2:30–4:30 aperitivolive

Tue–Sat aperitivo 2:30–4:30. Aperitivi $10–14 and snacks on the hosted PDF.

Cite: monteverdechicago.com · Updated 2026-09-02

West Looplive

Moneygun West Loop

Drink+foodTue–Fri 5–7 Waffletinilive

Tue–Fri 5–7. $10 tini’s with complimentary waffle fries.

Cite: moneygunchicago.com · Updated 2026-09-02

West Looplive

The Dearborn The Loop

Drink+foodMondays 4–6live

Mondays 4–6. $10 starters, wines, and Old Fashioneds; $12 martinis.

Cite: thedearborntavern.com · Updated 2026-09-02

The Looplive

Prime & Provisions The Loop

Drink+foodMon–Fri 4–6live

Mon–Fri 4–6 and Sunday 4–9. $1.50 oysters, $12 wine, half off bar bites.

Cite: primeandprovisions.com · Updated 2026-09-02

The Looplive

Big Star Wicker Park

Drink+foodMon–Thu 4–6live

Mon–Thu 4–6. $12 margarita, $8 ranch water, $4 Pacifico, ½ off nachos.

Cite: bigstarchicago.com · Updated 2026-09-02

Wicker Parklive

Estelle's Wicker Park

Window onlyMon–Fri 4–7 half-price drinkssoon

Mon–Fri 4–7 half-price drinks. No happy-hour dollar amounts on that page.

Cite: estelleschicago.com · Updated 2026-09-02

Wicker Parksoon

Cafe Ba-Ba-Reeba! Lincoln Park

Drink+foodDaily 4–6 at the barlive

Daily 4–6 at the bar. $1.50 pintxos, $3–5 tapas, $4 Estrella, $23 sangria pitchers.

Cite: cafebabareeba.com · Updated 2026-09-02

Lincoln Parklive