Pizzeria Portofino
One of the highest-rated tables near your stay.
4.9★ (18,498) · $$
SHORT BREAKS · ILLINOIS
Chicago,
assembled for you.
Lakefront, architecture and the best deep-dish-free food in the Midwest.Premium stays10
Local picks17
Trip length1–4 nights
WHAT WE DO
We assemble the whole trip.
You just show up.
No twenty browser tabs, no spreadsheet. Tell us how long you have, your budget and how you want to feel — Retreat48 plans the entire Chicago trip around it: how you get there, where you stay, the spa, dinner, a proper walk and the things worth doing. One trip, decided.
Assemble my Chicago trip- 01TravelDoor-to-door, the low-friction way
- 02Your stayQuality-checked, real spa, right for you
- 03Spa & wellnessTreatments and time that actually exist
- 04Food & pubsWhere to eat and drink, hand-picked
- 05Walks & things to doThe good stuff, none of the research
WHY CHICAGO
Lakefront, architecture and the best deep-dish-free food in the Midwest.
Chicago is a big city with a beach: the lakefront trail, the Art Institute, river cruises under the skyscrapers. Our stays are the grand and design hotels on the Magnificent Mile and in the Loop with spas and pools.
City breakCultureLakefront
PREMIUM STAYS
10 quality-checked stays in Chicago.
Hand-filtered for genuine quality — 4 and 5-star hotels with strong guest reviews and real facilities, spa included where it counts. Open any stay for live prices and to plan the whole trip around it.
5★ · quality-checked9The Ritz-Carlton, Chicago
Chicago · 202 reviewsView stay & live prices
5★ · quality-checked8.9The St. Regis Chicago
Chicago · 133 reviewsView stay & live prices
4★ · quality-checked9.4LondonHouse Chicago, Curio Collection by Hilton
Chicago · 1,790 reviewsView stay & live prices
4★ · quality-checked9.2Fairmont Chicago at Millennium Park Gold Experience
Chicago · 57 reviewsView stay & live prices
4★ · quality-checked9.1The LaSalle Chicago, Autograph Collection
Chicago · 309 reviewsView stay & live prices
4★ · quality-checked9Claridge House Chicago, Tapestry Collection by Hilton
Chicago · 1,162 reviewsView stay & live prices
4★ · quality-checked8.5InterContinental Chicago Magnificent Mile by IHG
Chicago · 1,064 reviewsView stay & live prices
4★ · quality-checked8.4Fairmont Chicago at Millennium Park
Chicago · 387 reviewsView stay & live prices
5★ · quality-checked9.2Sofitel Chicago Magnificent Mile
Chicago · 2,075 reviewsView stay & live prices
5★ · quality-checked9JW Marriott Chicago
Chicago · 411 reviewsView stay & live pricesWHILE YOU’RE THERE
The Chicago shortlist.
Hand-picked and quality-checked, the same way we choose your stay — a handful of places worth your limited hours, not a directory.
Aba
One of the highest-rated tables near your stay.
4.8★ (11,007) · $$$The Dearborn
One of the highest-rated tables near your stay.
4.7★ (10,042) · $$Au Cheval
One of the highest-rated tables near your stay.
4.7★ (12,934) · $$Quartino Ristorante
One of the highest-rated tables near your stay.
4.7★ (17,309) · $$Gathers Tea Bar
A top-rated café for a slow morning.
4.8★ (755) · $Beatrix
A top-rated café for a slow morning.
4.7★ (10,321) · $$BIÂN | A Luxury Private Club
A highly-rated spa a short hop from your stay.
4.8★ (42)Four Seasons Hotel Chicago
A highly-rated spa a short hop from your stay.
4.7★ (1,793)Soho House Chicago
A highly-rated spa a short hop from your stay.
4.6★ (1,749)Millennium Park
One of the area's most-loved things to do.
4.8★ (93,133)The Art Institute of Chicago
One of the area's most-loved things to do.
4.8★ (38,552)Chicago Riverwalk
One of the area's most-loved things to do.
4.8★ (22,951)Cloud Gate
One of the area's most-loved things to do.
4.7★ (41,054)Lincoln Park Conservatory
A local favourite for an unhurried hour outside.
4.8★ (4,155)Milton Lee Olive Park
A local favourite for an unhurried hour outside.
4.8★ (563)Maggie Daley Park
A local favourite for an unhurried hour outside.
4.7★ (8,639)GOOD QUESTIONS
Chicago, answered.
When is the best time to visit Chicago?
Chicago is a year-round city break. Spring and autumn give the best balance of decent weather and smaller crowds, while summer is liveliest and winter quietest.
How do I get to Chicago?
Chicago is usually reached by car, or by air into the nearest regional airport and a short drive on. Retreat48 works out the sensible route and real travel time from where you're starting.
What is Chicago best for?
Chicago is best for city break, culture and lakefront. Lakefront, architecture and the best deep-dish-free food in the Midwest.
READY WHEN YOU ARE
Stop researching. Start leaving.
Every stay we show has passed six independent checks. Everything around it — travel, food, walks, the plan — we assemble for you around your city, your budget and the feeling you’re after.
Assemble my Chicago trip