Signatures · checked 2026-09-03
Chicago happy hour has a house style: an Italian aperitivo, then a raw-bar or taco chaser. These are the signature sips and bites the venues print on their own pages — with prices only where the bar published them.
Sips the houses name
RPM Italian (52 W Illinois St, River North) posts weekdays in the bar 4–6 PM: signature cocktails $8 (RPM Spritz, Seasonal Old Fashioned, Crystal Paloma), wines by the glass $8 each, beer $5 (Peroni, Tivoli Outlaw), zero-proof $7. Bar Siena (832 W Randolph St, West Loop) posts Monday–Friday 3:30–5:30pm: cocktails $9 (Classic Martini, Espresso Martini, Paloma, Old Fashioned, Sicilian Lemon Drop Martini, Siena Smash) and wine $10. Cafe Ba-Ba-Reeba! (2024 N Halsted St, Lincoln Park) posts seven days a week 4–6 PM in the bar, first come first served: $4 Estrella Damm bottles, $23 sangria pitchers, La Hora Del Vermut 6, sangria glass 6, featured wine 6. Shaw's Crab House (21 E Hubbard St, River North) posts Monday–Friday 3–5 PM in the Oyster Bar: all draft beer 5, oyster wine of the month 8, Charles de Fere Brut 7, Cline Pinot Noir 9, Signature Mai Tai Martini 10, Shaw's Margarita 12, Old Fashioned 14. Big Star (1531 N Damen Ave, Wicker Park) posts Monday–Thursday 4–6 PM: Classic Margarita $12, Ranch Water $8, tequila and limeade or hibiscus agua fresca $8, Pacifico $4, shot of the day $3.
Bites worth crossing the river for
RPM Italian prints cicchetti $8 (tuna bruschetta, arancini, prosciutto bruschetta, pizzette, prime beef meatballs, stuffed peppers, mozzarella in carrozza) and Burrata & Spinach Raviolo $15. Bar Siena prints arancini $3 per piece, housemade sliders $4 each, bolognese fries $11, and Bufala Margherita and Burnt Pepperoni pizza $12. Cafe Ba-Ba-Reeba prints $1.50 pintxos with tapas from $3 to $5. Shaw's prints oysters half doz 12 / dozen 24, fish taco 5, crispy bites 8, garlic shrimp scampi 10, tuna on top roll 12, and mini lobster rolls 15. Big Star prints 1/2 off nachos.
| Venue | Window | Signature sip | Signature bite |
|---|---|---|---|
| RPM Italian | Weekdays 4–6 | $8 cocktails / $8 wine / $5 beer | $8 cicchetti |
| Bar Siena | Mon–Fri 3:30–5:30 | $9 cocktails / $10 wine | $4 sliders; $12 pizza |
| Cafe Ba-Ba-Reeba | Daily 4–6 | $4 Estrella / $23 pitchers | $1.50 pintxos |
| Shaw's | Mon–Fri 3–5 | $5 drafts; $10–$14 cocktails | Oysters 12 / $15 lobster rolls |
| Big Star | Mon–Thu 4–6 | $12 marg / $8 ranch water / $4 Pacifico | 1/2 off nachos |
How to run it
Start at Shaw's at 3 for the oyster bar. Move to Bar Siena by 3:30 for the $9 cocktail window. Land at RPM Italian at 4 for the $8 spritz, with Cafe Ba-Ba-Reeba's daily 4–6 as the any-day backup. Full windows live on Deals and On now.
Sources
- RPM Italian menus page (www.rpmrestaurants.com)
- Bar Siena happy hour menu (www.barsienawestloop.com)
- Cafe Ba-Ba-Reeba happy hour page (www.cafebabareeba.com)
- Shaw's weekday happy hour page (www.shawscrabhouse.com)
- Big Star happy hour menu (www.bigstarchicago.com)
Poured here: RPM Italian · Bar Siena · Cafe Ba-Ba-Reeba! · Shaw's Crab House · Big Star