Vacation Packages
Chicago Vacation Packages
Building a Chicago trip around an event? A package books the flight and the hotel together. Start with the date: the events on sale are listed below, with the airports and venues mapped so you can judge where to stay. On Expedia, enter Chicago as your destination.
How we earn: StubOrder may earn a commission when you book through the Expedia links on this page. It costs you nothing extra, and it never changes which events, venues or places we show you.
Chicago: the airport closest to downtown is Chicago Midway International Airport (MDW), 15 km (9 mi) from the city centre; ORD is 26 km (16 mi).
Pick your dates: upcoming Chicago events
The event fixes the trip. For an evening event, arrive the day before and fly home the morning after.
Chicago Architecture Foundation - River Cruise (Multiple Dates and Times)
Chicago Architecture Center, Chicago, Illinois
American League Division Series: Chicago White Sox vs. Cleveland Guardians - Home Game 1, Series Game 3
Rate Field, Chicago, Illinois
From about $273.00View TicketsThe Jungle Giants
Outset, Chicago, Illinois
From about $33.00View TicketsVidura Bandara Rajapaksa
Zanies Comedy Club - Chicago, Chicago, Illinois
Starbomb & Scoochie Boochie
Byline Bank Aragon Ballroom, Chicago, Illinois
From about $12.00View TicketsEpik High
House Of Blues - Chicago, Chicago, Illinois
From about $52.00View TicketsElizabeth Nichols
Carol's Pub, Chicago, Illinois
From about $176.00View TicketsMean Girls
Paramount Theatre - Aurora, Aurora, Illinois
From about $100.00View TicketsOperation Mincemeat
CIBC Theatre, Chicago, Illinois
From about $109.00View TicketsJekyll & Hyde
Broadway Playhouse at Water Tower Place, Chicago, Illinois
From about $95.00View Tickets
Airports serving Chicago
Which airport you fly into changes the rest of the trip. Distances are in a straight line from the city centre.
| Airport | Code | From the city centre |
|---|---|---|
| Chicago Midway International Airport | MDW | 15 km (9 mi) |
| Chicago O'Hare International Airport | ORD | 26 km (16 mi) |
Where the venues are
Stay near the venue you are going to, not just near the centre. Here is the nearest airport to each of the busiest Chicago venues.
| Venue | Nearest airport |
|---|---|
| Mainstage at Second City - Chicago | MDW, 17 km (11 mi) |
| Zanies Comedy Club - Chicago | MDW, 17 km (11 mi) |
| Orchestra Hall At Chicago Symphony Center | MDW, 15 km (9 mi) |
| United Center | MDW, 12 km (8 mi) |
| Lyric Opera House - IL | MDW, 14 km (9 mi) |
| Cadillac Palace | MDW, 15 km (9 mi) |
| Metropolis Performing Arts Centre | ORD, 13 km (8 mi) |
| City Winery - Chicago | MDW, 14 km (8 mi) |
Package or separate bookings?
A package keeps the trip in one booking and can cost less than buying the flight and the hotel apart. Booking separately gives you more choice: our Chicago hotels page sorts hotels by their real distance from the centre and from each venue, and our Chicago flights page searches live fares into the nearest airport.
Plan the rest of the trip
Frequently asked questions
Which airport is nearest Mainstage at Second City - Chicago?
MDW, 17 km (11 mi) away in a straight line. The table above has the nearest airport for the other big venues in Chicago.
Can I book the hotel on its own?
Yes. Our Chicago hotels page lists hotels by their real distance from the centre, and each venue has its own hotels page sorted by distance from that building.
Which airport is closest to downtown Chicago?
Chicago Midway International Airport (MDW) is 15 km (9 mi) from the city centre in a straight line; ORD is 26 km (16 mi).
Are event tickets part of a Chicago package?
No. A package covers the flight and the hotel. Buy your event tickets on StubOrder first, then book the package for the nights around the event.
