Everything you need for an unforgettable Chicago trip — skip-the-line tickets, airport transfers, hotels, car hire and cheap flights, all in one place.
Chicago is one of the world's most rewarding destinations — and planning your trip is simple when tickets, transfers, stays and flights all live in one place. Below you'll find hand-picked Chicago experiences and travel deals from trusted booking partners, refreshed regularly so you always see live availability and fair prices.
Browse every hotel in Chicago on Trip.com with today's real prices, guest reviews and free cancellation on most rooms.
The highest-rated 4 & 5-star hotels in Chicago
Price checked 4h ago · 1 night, 2 adults from Nov 29
#1Trip.com Price dropped −$6009.7/10Streeterville · Downtown Chicago
122 guest reviews
#2Trip.com Price dropped −$1009.7/10River North · Downtown Chicago
110 guest reviews
#3Trip.com Price dropped −$579.5/10Streeterville · Downtown Chicago
112 guest reviews
#4Trip.com Price dropped −$2049.4/10River North · Downtown Chicago
126 guest reviews
#5Trip.com Price dropped −$559.3/10West Loop · Near Puttery
102 guest reviews
#6Trip.com Price dropped −$839.2/10River North · Downtown Chicago
56 guest reviews
#7Trip.com Price dropped −$809.2/10Streeterville · Downtown Chicago
106 guest reviews
#8Trip.com9.2/10Chicago Loop · Downtown Chicago
123 guest reviews
Pick the neighbourhood that fits your trip, then compare live hotel prices.
Area photos: Wikimedia Commons (CC BY-SA)
Central, busy, office-heavy, transit-rich
Best for downtown attractions, Millennium Park, the riverwalk, and easy CTA access.
Browse Chicago hotels
Lively, upscale, restaurant-filled, nightlife-heavy
Close to the Magnificent Mile, the river, and multiple train lines, with many restaurants and hotels.
Hotels in River NorthTop hotels in River North
Top tours in River North
Polished, tourist-friendly, lakefront, convenient
Walk to Navy Pier, the Magnificent Mile, and the Museum of Contemporary Art, with easy lakefront access.
Hotels in Streeterville
Residential, leafy, relaxed, neighborhood-oriented
Near Lincoln Park Zoo, the Nature Museum, and the Red Line, offering an easy local feel with good transit.
Hotels in Lincoln ParkTop hotels in Lincoln Park
Top tours in Lincoln Park
Before you fly
Adjust your trip and the estimate updates instantly.
Nights
Travellers
Travel style
Currency
HotelTypical
4 nights × 1 room
Airport transfersTypical
Return trip × 1 car
Tours & ticketsTypical
4 days × 2 people
Food & drinksTypical
4 days × 2 people
Local transportTypical
4 days × 2 people
Estimated total
$1,291 per person
$2,582
Typical costs are researched estimates, refreshed monthly. "Live" prices come from current partner fares. Exchange rates update daily.
Tours, tickets and attractions
ExperiencesFree cancellation ChicagoGlide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers and Buckingham Fountain's spectacular light display. Hear lively commentary as you feel the night breeze and see Chicago’s skyline transformed into
ExperiencesInstant confirmation ChicagoFind tours, day trips and attraction tickets in Chicago with KKday — instant confirmation on most bookings.
View Deal ExperiencesSkip-the-line entry ChicagoMuseums, landmarks and top attractions in Chicago — instant mobile tickets with Tiqets, skip the queue.
View Deal ExperiencesBest-price guarantee ChicagoBook top tours, attractions and activities in Chicago with Klook — instant mobile tickets and a best-price guarantee.
View Deal Experiences ChicagoSkip-the-line tickets, day trips and tours in Chicago, with instant confirmation.
View Deal
ExperiencesFree cancellation ChicagoThe Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion wit
Experiences ChicagoThe Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and moder
ExperiencesFree cancellation ChicagoExperience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop ab
ExperiencesFree cancellation ChicagoExperience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Offic
ExperiencesFree cancellation ChicagoBe inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the C
ExperiencesFree cancellation ChicagoThe best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Michigan Avenue, the obs
ExperiencesFree cancellation ChicagoGet the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its shadowy history. If it’s raining/too hot the tour is almost all INDOOR. Led by a pa
Get from the airport to your hotel, hassle-free
TransferFixed price, no surge ChicagoPre-book a private airport transfer in Chicago with Kiwitaxi — fixed price, flight tracking and no surge pricing.
View DealHand-picked stays and live rates
HotelLive hotel prices ChicagoBrowse every hotel in Chicago with today's real prices, guest reviews and free-cancellation options.
Compare rental cars at great prices
CarFree cancellation ChicagoCompare rental cars from local and global suppliers in Chicago, with free cancellation on most bookings.
Live rates at O'Hare International Airport, from US$42/day. Change the dates to compare every partner.
Midsize car · or similar
Routes
via Trip.com
US$42/day
≈ US$126 for 3 days
Intermediate SUV · or similar
Routes
via Trip.com
US$44/day
≈ US$132 for 3 days
Small SUV · or similar
Thrifty
via Trip.com
US$67/day
≈ US$201 for 3 days
Standard SUV · or similar
Hertz
via Trip.com
US$67/day
≈ US$201 for 3 days
5 trusted brands side by side. Check two or three to get the best deal.
GetRentacar
Best for: Flexible bookingsCars · 10,000+ locations
from $40/day
Free cancellation
Trip.com
Best for: Big-brand airport rentalsCars · Worldwide airports
Free cancellation on most cars
| Brand | Best for | Vehicles | Coverage | Why book | Price | |
|---|---|---|---|---|---|---|
| QEEQ | Lowest price search | Cars | Worldwide | Low-price search | Live on site | Compare prices |
| Economybookings | All-inclusive pricing | Cars | 30,000+ locations | No hidden fees | Live on site | Compare prices |
| GetRentacar | Flexible bookings | Cars | 10,000+ locations | Free cancellation | from $40/day | Compare prices |
| Trip.com | Big-brand airport rentals | Cars | Worldwide airports | Free cancellation on most cars | Live on site | Compare prices |
| Localrent | Islands & local deals | Cars | Europe, Asia & islands | Local prices | Live on site | Compare prices |
Real plan prices from each brand, cheapest first, for plans that last your whole trip.
Prices checked under 1h ago on each brand's site. Prices may change at checkout.
The most popular Chicago experiences are skip-the-line attraction tickets, guided city tours and day trips. You can book them above with instant mobile tickets from trusted partners like Tiqets and Klook — no printing required.
A pre-booked private transfer is the easiest way to reach your Chicago hotel. You'll find fixed-price, meet-and-greet airport transfers in the section above, so there's no haggling with taxis when you land.
Chicago rewards visitors year-round, but the shoulder-season months usually offer the best mix of pleasant weather, thinner crowds and lower prices. Compare live hotel and flight prices above to find the cheapest dates for your trip.
Visa rules depend on your nationality and how long you stay, so always check your government's official travel advice before booking. Many travellers can enter visa-free or with a quick electronic authorisation.
Most travellers spend 3–5 days in Chicago to see the highlights without rushing. Booking your tours and transfers in advance helps you make the most of every day on the ground.
As featured on GKDeals
