Chicago is the great American city that Europeans tend to overlook, and they're missing out. This is where the skyscraper was born, and the skyline along Lake Michigan is still a jaw-dropper: Art Deco towers, glass giants and steel-framed classics, best seen from an architecture boat tour on the river. Add deep-dish pizza, blues clubs, world-class museums and sandy beaches right in the city, and you have one of the best city breaks in the States.
Almost everything visitors need sits in a compact downtown. The Loop, inside the circle of elevated 'L' tracks, has Millennium Park, the Art Institute and the theatres. North of the river, the Magnificent Mile runs past the department stores and grand hotels towards the leafy, moneyed Gold Coast, with River North's restaurants and bars to the west. Out near O'Hare, Rosemont is the airport base, and Gurnee, up towards Wisconsin, is the family day out.
The short answer

Best for first-timers
The Loop and Millennium Park
Millennium Park, the Art Institute and the river on your doorstep, with the L to everywhere else.

Best for luxury
The Magnificent Mile and Streeterville
The Peninsula, the Park Hyatt and the Four Seasons, high above the Magnificent Mile.

Best for nightlife
River North and the Riverwalk
Steakhouses, cocktail bars and rooftop terraces between the river and the Mag Mile.

Best for couples
The Gold Coast
Historic hotels on leafy streets, Oak Street boutiques and the lakeshore beach a few blocks away.

Best for families
Gurnee
Six Flags Great America and an indoor water park resort, an easy drive from the city.

Best for early flights
Rosemont
Hotels a few minutes from O’Hare, with free shuttles to the terminals.
Chicago areas at a glance
| Area | Best for | What it's like | Hotels |
|---|---|---|---|
| The Loop and Millennium Park | First-timers, Culture, Architecture | The Bean, the Art Institute and the city’s grand old hotels. | Hotels: 4 picked |
| The Magnificent Mile and Streeterville | Luxury, Shopping, Families | Department stores, the old Water Tower and the city’s top luxury hotels. | Hotels: 4 picked |
| River North and the Riverwalk | Nightlife, Food, First-timers | Steakhouses, galleries and riverside bars in the centre of everything. | Hotels: 4 picked |
| The Gold Coast | Couples, Shopping, Beach | Old money, Oak Street boutiques and the lakeshore on your doorstep. | Hotels: 4 picked |
| Rosemont and O'Hare | Early flights, Conventions, Concerts | Airport hotels with free shuttles, a short train ride from downtown. | Hotels: 27 |
| Gurnee | Families, Theme parks, Water parks | Rollercoasters, an indoor water park and outlet shopping north of the city. | Hotels: 10 |
The Loop and Millennium Park



- First-timers
- Culture
- Architecture
The Bean, the Art Institute and the city’s grand old hotels.
The Loop is Chicago's historic heart, named for the elevated 'L' tracks that circle it and rattle overhead. Millennium Park is its playground, with the mirrored Cloud Gate sculpture (everyone calls it the Bean), the Pritzker Pavilion's free summer concerts and the Art Institute next door. The Theater District glows at night, and the Riverwalk and architecture cruises are a short stroll north.
The hotels are some of the most beautiful in the country. The Chicago Athletic Association, in a converted Venetian Gothic gentlemen's club, sits right opposite Millennium Park. The Palmer House is a 19th-century institution with a ceiling of painted frescoes, and the Kimpton Gray turns a marble-clad office building into a stylish hotel with a bar styled like a law library. The Midland, in a Beaux Arts building, is close to the theatres.
Hotels to look at in The Loop and Millennium Park

★★★★
Chicago Athletic Association
Pets allowed · Parking
From £654 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
The Palmer House Hilton
Spa · Pool · Parking
From £386 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
Kimpton Gray Hotel
Pets allowed · Parking
From £441 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
The Midland Hotel, Chicago, A Tribute Portfolio
Spa · Parking
From £333 a night, taxes incl.2 adults · checked 1 Oct, 21:23
The Magnificent Mile and Streeterville



- Luxury
- Shopping
- Families
Department stores, the old Water Tower and the city’s top luxury hotels.
North Michigan Avenue, the Magnificent Mile, is Chicago's grand shopping boulevard, running from the river past the department stores and flagship shops to the castle-like Water Tower, one of the few buildings to survive the Great Fire of 1871. East of it, Streeterville stretches to the lake and Navy Pier, with its Ferris wheel, boat trips and summer fireworks.
Luxury hotels cluster here. The Peninsula is steps from the Water Tower with a spa and indoor pool, the Park Hyatt is an Art Deco beauty with an indoor pool and NoMI restaurant, and the InterContinental channels the glamour of the Roaring Twenties. For something different, the Sable sits right on Navy Pier with views of the lake and skyline, a hit with families.
Hotels to look at in The Magnificent Mile and Streeterville

★★★★★
The Peninsula Chicago
Spa · Pool · Parking
From £1,099 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
Sable At Navy Pier Chicago Curio Collection Hilton
Parking
From £458 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★★
Park Hyatt Chicago
Spa · Pool · Pets allowed
From £869 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
DoubleTree by Hilton Chicago - Magnificent Mile
Beach 200 m · All-inclusive option · Spa
From £297 a night, taxes incl.2 adults · checked 1 Oct, 21:23
River North and the Riverwalk



- Nightlife
- Food
- First-timers
Steakhouses, galleries and riverside bars in the centre of everything.
River North sits between the Chicago River and the Magnificent Mile, and it's where the city goes out. Old warehouses hold art galleries, steakhouses and deep-dish pizza joints, and the bars range from rooftop terraces to speakeasies. Below, the Riverwalk lines the water with cafés and wine bars, and the architecture cruises depart from here.
It's perfectly placed between the Loop and the Mag Mile. The Royal Sonesta River North has a heated indoor pool and a rooftop sundeck, the Westin River North is a ten-minute walk from the Chicago Theatre, and L7 is a boutique hotel steps from the Riverwalk. The all-glass Swissôtel, designed by Chicago architect Harry Weese, has wrap-around views from Navy Pier to Millennium Park.
Hotels to look at in River North and the Riverwalk

★★★★
Royal Sonesta Chicago River North
Pool · Family-friendly · Pets allowed
From £778 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
Westin Chicago River North
Family-friendly · Parking
From £543 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
L7 Chicago By Lotte
Pets allowed · Parking
From £528 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
Swissotel Chicago
Family-friendly · Parking
From £320 a night, taxes incl.2 adults · checked 1 Oct, 21:23
The Gold Coast



- Couples
- Shopping
- Beach
Old money, Oak Street boutiques and the lakeshore on your doorstep.
At the northern end of the Magnificent Mile, the Gold Coast is Chicago's most elegant neighbourhood: tree-lined streets of brownstones and mansions, designer boutiques on Oak Street, and the bars and steakhouses of Rush Street. Oak Street Beach, where the city's sand meets Lake Michigan, is a few blocks away.
The Drake has been the grande dame where the Magnificent Mile begins since 1920. The Waldorf Astoria brings Parisian style, with fireplaces or private terraces and a lap pool in its spa. The Whitehall is a charming historic hotel half a block from Michigan Avenue, and the Viceroy is a sleek option near the Oak Street shops. Romantic, refined and a little calmer than downtown proper.
Hotels to look at in The Gold Coast

★★★★
The Drake
Parking
From £417 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★★
Waldorf Astoria Chicago
Spa · Pool · Parking
From £938 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
The Whitehall Hotel BW Premier Collection
Beach 480 m · Parking
From £288 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
Viceroy Chicago
Pool · Parking
From £755 a night, taxes incl.2 adults · checked 1 Oct, 21:23
Rosemont and O'Hare



- Early flights
- Conventions
- Concerts
Airport hotels with free shuttles, a short train ride from downtown.
Rosemont sits right beside O'Hare, one of the world's busiest airports, and it's packed with airport hotels. It has its own entertainment district, the Donald E. Stephens Convention Center and Allstate Arena nearby, and the Blue Line 'L' runs straight into downtown.
The DoubleTree and the Embassy Suites face the convention centre, and both are just minutes from the airport; the Embassy Suites runs its shuttle from 4am to midnight. The Rose is a pet-friendly boutique hotel with triple-glazed windows to keep the planes out, and the Sheraton is a reliable choice. Stay here for flights and events; stay downtown for the city.
Hotels to look at in Rosemont

★★★★
Doubletree Hotel Chicago O'Hare Airport-Rosemont
Pets allowed · Parking
From £149 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
Embassy Suites by Hilton Chicago O'Hare Rosemont
Spa · Pool · Pets allowed
From £173 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
The Rose Chicago, Tapestry Collection by Hilton
Pets allowed · Parking
From £260 a night, taxes incl.2 adults · checked 1 Oct, 21:23

★★★★
Sheraton Chicago O'Hare Airport Hotel
Parking
From £218 a night, taxes incl.2 adults · checked 1 Oct, 21:23
Gurnee



- Families
- Theme parks
- Water parks
Rollercoasters, an indoor water park and outlet shopping north of the city.
About an hour north of downtown, on the road to Wisconsin, Gurnee is Chicagoland's family playground. Six Flags Great America has the region's biggest rollercoasters, and Great Wolf Lodge is a huge resort with an indoor water park that works whatever the weather, a real bonus in a Chicago winter.
The Hampton Inn is right across the road from Six Flags, and WoodSpring Suites is a budget-friendly option for longer stays. It's not a base for exploring the city, but for a few days of thrills tacked onto a Chicago break, it's ideal.
Hotels to look at in Gurnee
Which area?
First visit? Stay in the Loop or River North and walk to almost everything. Luxury and shopping? The Magnificent Mile or the Gold Coast. Foodies should also explore the West Loop, Chicago's hottest restaurant district, a short ride from downtown. Flying out early? Rosemont, next to O'Hare.
Getting around
Downtown is compact and walkable, and the 'L' trains are quick and cheap; the Blue Line runs from O'Hare and the Orange Line from Midway straight into the Loop. Winters are bitterly cold and windy, so a hotel close to the sights matters more from December to March. Summer is festival season, when the lakefront comes alive.
Questions about where to stay in Chicago
- What is the best area to stay in Chicago?
- For a first visit, the Loop or River North, both within walking distance of Millennium Park, the Art Institute, the Riverwalk and the Magnificent Mile. For luxury and shopping, choose the Magnificent Mile or the Gold Coast.
- Is it better to stay in the Loop or on the Magnificent Mile?
- The Loop is best for culture, architecture and theatres, and has handsome historic hotels, but it is quieter at night. The Magnificent Mile has the shops, Navy Pier and most of the big luxury hotels, and is livelier in the evenings.
- Where should families stay in Chicago?
- Streeterville and the Magnificent Mile are great for families, close to Navy Pier, the lakefront and the beaches, with hotels that have indoor pools. For theme parks, Gurnee has Six Flags Great America and Great Wolf Lodge’s indoor water park.
- Where is the nightlife in Chicago?
- River North has the densest concentration of bars, clubs and restaurants downtown, and Rush Street in the Gold Coast is lively too. Further out, Wicker Park and the West Loop are popular with locals.
- Which part of downtown Chicago is quietest?
- The Gold Coast’s residential side streets are the calmest part of central Chicago, and the Loop empties out in the evenings once office workers head home.
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